Pesticidally active azetidine sulfones amide isoxazoline derivatives

ABSTRACT

Compounds of formula (I) wherein the substituents are as defined in claim  1 , and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides and can be prepared in a manner known per se.

The present invention relates to pesticidally active, in particularinsecticidally active, azetidine sulfonamide isoxazolines, tocompositions comprising those compounds, and to their use forcontrolling animal pests (including arthropods and in particular insectsor representatives of the order Acarina).

Certain isoxazoline derivatives with insecticidal properties aredisclosed, for example, in WO2011067272.

There have now been found novel pesticidally active azetidinesulfonamide isoxazoline derivatives.

The present invention accordingly relates to compounds of formula (I)

whereinA¹, A², A³ and A⁴, independently of one another, are C—H, C—R⁵ ornitrogen;R¹ is hydrogen, C₁-C₈alkyl, C₁-C₈alkylcarbonyl-, C₁-C₈alkoxy,C₁-C₈alkoxy-C₁-C₈alkyl or C₁-C₈alkoxycarbonyl;R² is C₁-C₈alkyl or C₁-C₈haloakyl;R³ is C₁-C₈haloalkyl;R⁴ is aryl, aryl substituted by one to three R⁷, heteroaryl orheteroaryl substituted by one to three R⁷; each R⁵ is independentlyhalogen, cyano, nitro, C₁-C₈alkyl, C₃-C₈cycloalkyl, C₁-C₈haloalkyl,C₂-C₈alkenyl, C₂-C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl,C₁-C₈alkoxy, C₁-C₈haloalkoxy, or C₁-C₈alkoxycarbonyl-, or two R⁵ onadjacent carbon atoms together form a —CH₂—CH₂—CH₂— bridge, a—CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge; andeach R⁷ is independently halogen, cyano, nitro, C₁-C₈alkyl,C₁-C₈haloalkyl, C₁-C₈alkoxy or C₁-C₈haloalkoxy;and agrochemically acceptable salts, stereoisomers, enantiomers,tautomers and N-oxides of those compounds.

Compounds of formula (I) which have at least one basic centre can form,for example, acid addition salts, for example with inorganic acids suchas mineral acids, for example perchloric acid, sulfuric acid, nitricacid, a phosphorus acid or a hydrohalic acid, with organic carboxylicacids, such as C₁-C₄alkanecarboxylic acids which are unsubstituted orsubstituted, for example by halogen, for example acetic acid ortrifluoroacetic acid, such as saturated or unsaturated dicarboxylicacids, for example oxalic acid, malonic acid, succinic acid, maleicacid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids,for example ascorbic acid, lactic acid, malic acid, tartaric acid orcitric acid, or such as benzoic acid, or with organic sulfonic acids,such as C₁-C₄alkane- or arylsulfonic acids which are unsubstituted orsubstituted, for example by halogen, for example methane- orp-toluenesulfonic acid. Compounds of formula (I) which have at least oneacidic group can form, for example, salts with bases, for examplemineral salts such as alkali metal or alkaline earth metal salts, forexample sodium, potassium or magnesium salts, or salts with ammonia oran organic amine, such as morpholine, piperidine, pyrrolidine, a mono-,di- or tri-lower-alkylamine, for example ethyl-, diethyl-, triethyl- ordimethylpropylamine, or a mono-, di- or trihydroxy-lower-alkylamine, forexample mono-, di- or triethanolamine.

Where substituents are indicated as being substituted, this means thatthey carry one or more identical or different substituents, e.g. one tothree substituents. Where a group is indicated as being substituted,e.g. alkyl, this includes those groups that are part of other groups,e.g. the alkyl in alkoxy or phenyl in phenyloxy. The number ofsubstituents does not exceed the number of available C—H and N—H bonds.

The alkyl groups occurring in the definitions of the substituents can bestraight-chain or branched and are, but are not limited to, methyl,ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl,pentyl, hexyl, nonyl, decyl and their branched isomers. Alkylsulfanyl,alkylsulfinyl, alkylsulfonyl, alkoxy, alkenyl and alkynyl radicals arederived from the alkyl radicals mentioned. The alkenyl and alkynylgroups can be mono- or polyunsaturated.

Halogen is generally fluorine, chlorine, bromine or iodine. This alsoapplies, correspondingly, to halogen in combination with other meanings,such as haloalkyl or halophenyl.

Haloalkyl groups preferably have a chain length of from 1 to 6 carbonatoms. Haloalkyl is, but is not limited to, fluoromethyl,difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl,trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl,pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl,2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl.

Alkoxy is, but is not limited to, methoxy, ethoxy, propoxy, i-propoxy,n-butoxy, isobutoxy, sec-butoxy and tert-butoxy and also the isomericpentyloxy and hexyloxy radicals.

Alkoxyalkyl is, but are not limited to, methoxymethyl, methoxyethyl,ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl,isopropoxymethyl or isopropoxyethyl.

Alkoxycarbonyl is, but are not limited to, methoxycarbonyl (which isC₁alkoxycarbonyl), ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl,n-butoxycarbonyl, tert-butoxycarbonyl, n-pentoxycarbonyl orhexoxycarbonyl.

The cycloalkyl groups preferably have from 3 to 6 ring carbon atoms andare, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

As used herein, the term “C₂-C₈alkynyl” refers to a straight or branchedhydrocarbon chain radical group consisting solely of carbon and hydrogenatoms, containing at least one triple bond, having from two to eightcarbon atoms, and which is attached to the rest of the molecule by asingle bond. Examples of C₂-C₈ alkynyl include, but are not limited to,ethynyl, prop-1-ynyl, but-1-ynyl and but-2-ynyl.

As used herein, the term “C₂-C₈alkenyl” refers to a straight or branchedhydrocarbon chain radical group consisting solely of carbon and hydrogenatoms, containing at least one double bond, having from two to eightcarbon atoms, and which is attached to the rest of the molecule by asingle bond. Examples of C₂-C₈alkenyl include, but are not limited to,prop-1-enyl, but-1-enyl and but-2-enyl.

Aryl means a six to fourteen membered aromatic carbocyclic ring systemwhich can be mono-, bi- or tricyclic. Examples of such rings includephenyl, indenyl, naphthalenyl, anthranyl, or phenanthrenyl. A preferredaryl group is phenyl.

Heteroaryl stands for a five to six membered aromatic ring systemcomprising 1 to 3 hetero atoms selected from the group consisting ofnitrogen, oxygen and sulfur, it not being possible for the ring systemto contain more than 2 oxygen atoms or more than 2 sulfur atoms.Examples of heteroaryl are furyl, thienyl, pyrrolyl, imidazolyl,pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl,thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl,pyrazinyl. A preferred heteroaryl group is pyridyl.

The compounds of formula I according to the invention also includehydrates which may be formed during the salt formation. Preferably thepresent invention accordingly relates to compounds of formula (I)

whereinA¹, A², A³ and A⁴, independently of one another, are C—H, C—R⁵ ornitrogen;R¹ is hydrogen, C₁-C₈alkyl, C₁-C₈alkylcarbonyl-, C₁-C₈alkoxy,C₁-C₈alkoxy-C₁-C₈alkyl or C₁-C₈alkoxycarbonyl;R² is C₁-C₈alkyl or C₁-C₈haloakyl;R³ is C₁-C₈haloalkyl;R⁴ is six to fourteen membered aryl, six to fourteen membered arylsubstituted by one to three R⁷ or five to six membered heteroaryl whichcan be substituted by one or more R⁷ and which comprises 1 to 3heteroatoms selected from the group consisting of nitrogen, oxygen andsulfur, it not being possible for the ring system to contain more than 2oxygen atoms or more than 2 sulfur atoms; each R⁵ is independentlyhalogen, cyano, nitro, C₁-C₈alkyl, C₃-C₈cycloalkyl, C₁-C₈haloalkyl,C₂-C₈alkenyl, C₂-C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl,C₁-C₈alkoxy, C₁-C₈haloalkoxy, or C₁-C₈alkoxycarbonyl-, or two R⁵ onadjacent carbon atoms together form a —CH₂—CH₂—CH₂— bridge, a—CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge; andeach R⁷ is independently halogen, cyano, nitro, C₁-C₈alkyl,C₁-C₈haloalkyl, C₁-C₈alkoxy or C₁-C₈haloalkoxy;and agrochemically acceptable salts, stereoisomers, enantiomers,tautomers and N-oxides of those compounds.Preferably at least two of A¹, A², A³ and A⁴ are different fromnitrogen.Preferably A¹ is C—H or C—R⁵; more preferably A¹ is C—R⁵.Preferably A² is C—H or C—R⁵; more preferably A² is C—H.Preferably A³ is C—H or N; more preferably A³ is C—H.Preferably A⁴ is C—H or N; more preferably A⁴ is C—H.More preferably A¹ is C—R⁵, and A², A³ and A⁴ are C—H.

EMBODIMENT E1

In a preferred embodiment of the invention,R¹ is hydrogen, C₁-C₈alkyl, C₁-C₈alkylcarbonyl- or C₁-C₈alkoxycarbonyl;more preferably R¹ is hydrogen, methyl, ethyl, methylcarbonyl-,ethylcarbonyl-, t-butylcarbonyl-, isopropycarbonyl-, ethoxycarbonyl ormethoxycarbonyl; more preferably R¹ is hydrogen, methyl, ethyl,methylcarbonyl-, or methoxycarbonyl; more preferably R¹ is hydrogen,methyl or ethyl; more preferably R¹ is hydrogen, methylcarbonyl-, ormethoxycarbonyl; more preferably R¹ is hydrogen or methyl; morepreferably R¹ is hydrogen or methoxycarbonyl; most preferably R¹ ishydrogen.

EMBODIMENT E2

In a preferred embodiment of the invention,preferably R² is C₁-C₄alkyl or C₁-C₄haloalkyl; more preferably R² ismethyl, ethyl, propyl, isopropyl, CH₂F, CH₂Cl, CH₂Br, CHF₂, CF₃,CH₂CH₂CF₃ or CH₂CF₃; especially R² is methyl, ethyl, CH₂F, CH₂Cl, CH₂Bror CHF₂.

EMBODIMENT E3

In a preferred embodiment of the invention,preferably R³ is C₁-C₄haloalkyl; more preferably R³ ischlorodifluoromethyl or trifluoromethyl; most preferably R³ istrifluoromethyl.

EMBODIMENT E4

In a preferred embodiment of the invention,preferably R⁴ is six to fourteen membered aryl, six to fourteen memberedaryl substituted by one to three R⁷ or five to six membered heteroarylwhich can be substituted by one or more R⁷ and which comprises 1 to 3heteroatoms selected from the group consisting of nitrogen, oxygen andsulfur, it not being possible for the ring system to contain more than 2oxygen atoms or more than 2 sulfur atoms; more preferably R⁴ is six tofourteen membered aryl or six to fourteen membered aryl substituted byone to three R⁷; most preferably R⁴ is phenyl or phenyl substituted byone to three R⁷; even more preferably R⁴ is phenyl substituted by one tothree R⁷; especially R⁴ is 3,5-bis-(trifluoromethyl)-phenyl,3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl,3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl,3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl,3,5-dichloro-4-fluoro-phenyl or 3,4,5-trichloro-phenyl; more especiallyR⁴ is 3-chloro-5-trifluoromethyl-phenyl, 3,5-dichloro-phenyl,3,5-bis-(trifluoromethyl)-phenyl, 3,5-dichloro-4-fluoro-phenyl, or3,4,5-trichloro-phenyl.

EMBODIMENT E5

In a preferred embodiment of the invention,preferably each R⁵ is independently halogen, cyano, nitro, C₁-C₈alkyl,C₃-C₈cycloalkyl, C₁-C₈haloalkyl, or C₂-C₈alkenyl, or two R⁵ on adjacentcarbon atoms together form a —CH₂—CH₂—CH₂— bridge or a —CH═CH—CH═CH—bridge; more preferably each R⁵ is independently halogen, cyano, nitro,C₁-C₈alkyl, C₂-C₈ alkenyl, C₃-C₈cycloalkyl, C₁-C₈haloalkyl, or two R⁵ onadjacent carbon atoms together form a —CH₂—CH₂—CH₂— bridge or a—CH═CH—CH═CH— bridge; even more preferably each R⁵ is independentlybromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl,cyclopropyl, vinyl or two R⁵ on adjacent carbon atoms together form a—CH₂—CH₂—CH₂— bridge or a —CH═CH—CH═CH— bridge; yet even more preferablyeach R⁵ is independently bromo, chloro, ethyl, cyclopropyl,trifluoromethyl, vinyl, methyl, or two R⁵ on adjacent carbon atomstogether form a —CH₂—CH₂—CH₂— bridge or a —CH═CH—CH═CH— bridge; mostpreferably each R⁵ is independently chloro, bromo, trifluoromethyl,ethyl, methyl, or two R⁵ on adjacent carbon atoms together form a—CH₂—CH₂—CH₂— bridge; most especially each R⁵ is methyl or two R⁵ onadjacent carbon atoms together form a —CH₂—CH₂—CH₂— bridge.

EMBODIMENT E6

In a preferred embodiment of the invention,preferably each R⁷ is independently halogen, cyano, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy or C₁-C₄haloalkoxy; more preferably each R⁷is methyl, fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy,cyano or methoxy, even more preferably each R⁷ is Cl, Br, F, or CF₃;Each of the Embodiments E1 to E6 can be combined to a new preferredgroup of compounds of formula (I) as shown in the following Table E.

TABLE E preferred embodiments of the formula (I): CombinationCombination Combination Combination Combination E1 + E2 E1 + E6 E3 +E4 + E5 E2 + E5 + E6 E2 + E3 + E4 + E6 E1 + E3 E2 + E6 E1 + E2 + E4 E3 +E4 + E6 E2 + E4 + E5 + E6 E2 + E3 E3 + E6 E1 + E3 + E4 E3 + E5 + E6 E3 +E4 + E5 + E6 E1 + E4 E4 + E6 E2 + E3 + E4 E1 + E2 + E3 + E6 E1 + E2 +E3 + E5 E2 + E4 E5 + E6 E1 + E2 + E6 E1 + E2 + E4 + E6 E1 + E2 + E4 + E5E3 + E4 E1 + E2 + E5 E1 + E3 + E6 E1 + E2 + E5 + E6 E1 + E3 + E4 + E5E1 + E5 E1 + E3 + E5 E1 + E4 + E6 E1 + E3 + E4 + E6 E2 + E3 + E4 + E5E2 + E5 E1 + E4 + E5 E1 + E5 + E6 E1 + E3 + E5 + E6 E1 + E2 + E3 + E4 +E5 E3 + E5 E2 + E3 + E5 E2 + E3 + E6 E1 + E4 + E5 + E6 E1 + E2 + E3 +E4 + E5 + E6 E4 + E5 E2 + E4 + E5 E2 + E4 + E6 E2 + E3 + E5 + E6In all of the preferred embodiments mentioned above and the combinationsof Table E, A¹ is preferably C—CH₃, A² is preferably C—H, A³ ispreferably C—H and A⁴ is preferably C—H.In a more preferred embodiment of the invention in the compounds of theformula (I)A¹ is C—R⁵, A², A³ and A⁴ are C—H;R¹ is hydrogen;R² is methyl, ethyl, propyl, isopropyl, CH₂F, CH₂Cl or CHF₂;R³ is trifluoromethyl;R⁴ is phenyl substituted by one to three R⁷; especially R⁴ is3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl,3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl,3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl,4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or3,4,5-trichloro-phenyl; more especially R⁴ is3-chloro-5-trifluoromethyl-phenyl, 3,5-dichloro-phenyl,3,5-bis-(trifluoromethyl)-phenyl, 3,5-dichloro-4-fluoro-phenyl, or3,4,5-trichloro-phenyl;R⁵ is chloro, bromo, trifluoromethyl, ethyl or methyl;each R⁷ is independently Cl, Br, F, or CF₃; In a even more preferredembodiment of the invention in the compounds of the formula (I) A¹ isC—R⁵, A², A³ and A⁴ are C—H;R¹ is hydrogen;R² is methyl, ethyl, propyl, isopropyl, CH₂F, CH₂Cl or CHF₂;R³ is trifluoromethyl;R⁴ is phenyl substituted by one to three R⁷; especially R⁴ is3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl,3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl,3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl,4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro-phenyl or3,4,5-trichloro-phenyl; more especially R⁴ is3-chloro-5-trifluoromethyl-phenyl, 3,5-dichloro-phenyl,3,5-bis-(trifluoromethyl)-phenyl, 3,5-dichloro-4-fluoro-phenyl, or3,4,5-trichloro-phenyl;R⁵ is methyl;each R⁷ is independently Cl, Br, F, or CF₃;The compounds of the invention may be made by a variety of methods asshown in Schemes 1 to 4.

1) Compounds of formula (Ic), wherein R⁶ is S(O)₂R², hydrogen or anamine protecting group (usual removable amine protecting groups aredescribed in “Greene's Protective Groups in Organic Synthesis”, 4th ed.,Wuts, P. G. M., Greene, T. W. 2007, J. Wiley, Hoboken, N.J.), can beprepared by reacting a compound of formula (II) wherein R is OH,C₁-C₆alkoxy or Cl, F or Br, with an amine of formula (III), as shown inScheme 1. When R is OH such reactions are usually carried out in thepresence of a coupling reagent, such as N,N′-dicyclohexylcarbodiimide(“DCC”), 1-ethyl-3-(3-dimethylamino-propyl)carbodiimide hydrochloride(“EDC”) or bis(2-oxo-3-oxazolidinyl)phosphonic chloride (“BOP-Cl”), inthe presence of a base, and optionally in the presence of a nucleophiliccatalyst, such as hydroxybenzotriazole (“HOBT”). When R is Cl, suchreactions are usually carried out in the presence of a base, andoptionally in the presence of a nucleophilic catalyst. Alternatively, itis possible to conduct the reaction in a biphasic system comprising anorganic solvent, preferably ethyl acetate, and an aqueous solvent,preferably a solution of sodium hydrogen carbonate. When R isC₁-C₆alkoxy it is sometimes possible to convert the ester directly tothe amide by heating the ester and amine together in a thermal process.Suitable bases include pyridine, triethylamine,4-(dimethylamino)-pyridine (“DMAP”) or diisopropylethylamine (Hunig'sbase). Preferred solvents are N,N-dimethylacetamide, tetrahydrofuran,dioxane, 1,2-dimethoxyethane, ethyl acetate and toluene. The reaction iscarried out at a temperature of from 0° C. to 100° C., preferably from15° C. to 30° C., in particular at ambient temperature. Amines offormula (III) are either known in the literature or can be preparedusing methods known to a person skilled in the art.2) Acid halides of formula (II), wherein R is Cl, F or Br, may be madefrom carboxylic acids of formula (II), wherein R is OH, under standardconditions, as described for example in WO 2009/080250.3) Carboxylic acids of formula (II), wherein R is OH, may be formed fromesters of formula (II), wherein R is C₁-C₆alkoxy as described forexample in WO 2009/080250.4) Compounds of formula (Ic) can be prepared by reacting a compound offormula (IV) wherein X^(B) is a leaving group, for example a halogen,such as bromo, with carbon monoxide and an amine of formula (III), inthe presence of a catalyst, such as palladium(II) acetate orbis(triphenylphosphine)palladium(II) dichloride, optionally in thepresence of a ligand, such as triphenylphosphine, and a base, such assodium carbonate, pyridine, triethylamine, 4-(dimethylamino)-pyridine(“DMAP”) or diisopropylethylamine (Hunig's base), in a solvent, such aswater, N,N-dimethylformamide or tetrahydrofuran. The reaction is carriedout at a temperature of from 50° C. to 200° C., preferably from 100° C.to 150° C. The reaction is carried out at a pressure of from 50 to 200bar, preferably from 100 to 150 bar.5) Compounds of formula (IV) wherein X^(B) is a leaving group, forexample a halogen, such as bromo, can be made by a various of methods,for example as described in WO 2009/080250.

6) Alternatively, compounds of formula (Ic), wherein R⁶ is S(O)₂R²,hydrogen or an amine protecting group (usual removable amine protectinggroups are described in “Greene's Protective Groups in OrganicSynthesis”, 4th ed., Wuts, P. G. M., Greene, T. W. 2007, J. Wiley,Hoboken, N.J.), can be prepared by various methods from an intermediateof formula (V) as shown in Scheme 2 wherein X^(B) is a leaving group,for example a halogen, such as bromo, or X^(B) is cyano, formyl oracetyl according to similar methods to those described in WO2009/080250. An intermediate of formula (V) can be prepared for examplefrom an intermediate of formula (VI) as described in the same reference.

7) Alternatively, compounds of formula (Ic) can be prepared by variousmethods from an intermediate of formula (VII) as shown in Scheme 3wherein X^(C) is CH═C(R³)R⁴, or CH₂C(OH)(R³)R⁴ wherein R³ and R⁴ are asdefined for a compound of formula (I) according to similar methods tothose described in WO 2009/080250.8) Compounds of formula (VII) wherein X^(C) is CH═C(R³)R⁴, orCH₂C(OH)(R³)R⁴ can be prepared from a compound of formula (Va) or from acompound of formula (VII) wherein X^(C) is CH₂-halogen using similarmethods to those described in WO 2009/080250.9) Compounds of formula (VII) wherein X^(C) is CH₂-halogen, such asbromo or chloro, can be prepared by reacting a methyl ketone of formula(Va), with a halogenating agent, such as bromine or chlorine, in asolvent, such as acetic acid, at a temperature of from 0° C. to 50° C.,preferably from ambient temperature to 40° C.

10) Compounds of formula (Ia) can be prepared by reacting a compound offormula (Ib) with a sulfonyl compound of formula (VIII), wherein LG is asuitable leaving group, such as a halogen atom, such as chlorine, or animidazole or a substituted phenoxy group, as shown in Scheme 4. Suchreactions are usually carried out in the absence or in the presence of abase, such as sodium hydroxide, trimethylamine, sodiumhydrogenocarbonate, sodium carbonate, using methods known to a personskilled in the art.11) In addition, compounds of formula (Ib) can be prepared bydeprotecting the amine in a compound of formula (Ic), where PG is anamine protecting group (removable protecting groups are described in“Greene's Protective Groups in Organic Synthesis”, 4th ed., Wuts, P. G.M., Greene, T. W. 2007, J. Wiley, Hoboken, N.J.) as shown in Scheme 4.Such reactions are known to a person skilled in the art. The reactantscan be reacted in the presence of a base. Examples of suitable bases arealkali metal or alkaline earth metal hydroxides, alkali metal oralkaline earth metal hydrides, alkali metal or alkaline earth metalamides, alkali metal or alkaline earth metal alkoxides, alkali metal oralkaline earth metal acetates, alkali metal or alkaline earth metalcarbonates, alkali metal or alkaline earth metal dialkylamides or alkalimetal or alkaline earth metal alkylsilylamides, alkylamines,alkylenediamines, free or N-alkylated saturated or unsaturatedcycloalkylamines, basic heterocycles, ammonium hydroxides andcarbocyclic amines. Examples which may be mentioned are sodiumhydroxide, sodium hydride, sodium amide, sodium methoxide, sodiumacetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide,potassium carbonate, potassium hydride, lithium diisopropylamide,potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine,diisopropylethylamine, triethylenediamine, cyclohexylamine,N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine,4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine,benzyltrimethylammonium hydroxide and 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU). The reactants can be reacted with each other as such, i.e.without adding a solvent or diluent. In most cases, however, it isadvantageous to add an inert solvent or diluent or a mixture of these.If the reaction is carried out in the presence of a base, bases whichare employed in excess, such as triethylamine, pyridine,N-methylmorpholine or N,N-diethylaniline, may also act as solvents ordiluents.

The reaction is advantageously carried out in a temperature range fromapproximately −80° C. to approximately +140° C., preferably fromapproximately −30° C. to approximately +100° C., in many cases in therange between ambient temperature and approximately +80° C.

A compound of formula (I) can be converted in a manner known per se intoanother compound of formula (I) by replacing one or more substituents ofthe starting compound of formula (I) in the customary manner by(an)other substituent(s) according to the invention.

Depending on the choice of the reaction conditions and startingmaterials which are suitable in each case, it is possible, for example,in one reaction step only to replace one substituent by anothersubstituent according to the invention, or a plurality of substituentscan be replaced by other substituents according to the invention in thesame reaction step.

The present invention also provides intermediates useful for thepreparation of compounds of formula (I). Certain intermediates are noveland as such form a further aspect of the invention. One group of novelintermediates are compounds of formula (Int-1)

wherein A¹, A², A³, A⁴ and R¹ are as defined for a compound of formula(I) and R⁶ is hydrogen or S(O)₂R² and X^(B) is a halogen, such as bromo,or X^(B) is cyano, formyl, CH═N—OH or acetyl; and a salt or N-oxidethereof. The preferences for A¹, A², A³, A⁴, R² and R¹ are the same asthe preferences set out for the corresponding substituents of a compoundof formula (I).

Another group of novel intermediates are compounds of formula (Int-II)

wherein A¹, A², A³, A⁴ and R¹ are as defined for a compound of formula(I); R⁶ is hydrogen or S(O)₂R² and X^(C) is CH₂-halogen, wherein halogenis e.g. bromo or chloro, CH═C(R³)R⁴ or CH₂C(OH)(R³)R⁴ wherein R³ and R⁴are as defined for a compound of formula (I); and a salt or N-oxidethereof. The preferences for A¹, A², A³, A⁴, R², R³, R⁴ and R¹ are thesame as the preferences set out for the corresponding substituents of acompound of formula (I).

Another group of novel intermediates are compounds of formula (Int-III)

wherein A¹, A², A³, A⁴, R¹, R³ and R⁴ are as defined for a compound offormula (I) and R⁶ is hydrogen or an amine protecting group, such as aboc group (removable protecting groups are described in “Greene'sProtective Groups in Organic Synthesis”, 4th ed., Wuts, P. G. M.,Greene, T. W. 2007, J. Wiley, Hoboken, N.J.) and a salt or N-oxidethereof. The preferences for A¹, A², A³, A⁴, R¹, R³ and R⁴ are the sameas the preferences set out for the corresponding substituents of acompound of formula (I).

The compounds of formula (I) and, where appropriate, the tautomer'sthereof, in each case in free form or in salt form, can be present inthe form of one of the isomers which are possible or as a mixture ofthese, for example in the form of pure isomers, such as antipodes and/ordiastereomers, or as isomer mixtures, such as enantiomer mixtures, forexample racemates, diastereomer mixtures or racemate mixtures, dependingon the number, absolute and relative configuration of asymmetric carbonatoms which occur in the molecule and/or depending on the configurationof non-aromatic double bonds which occur in the molecule; the inventionrelates to the pure isomers and also to all isomer mixtures which arepossible and is to be understood in each case in this sense hereinaboveand hereinbelow, even when stereochemical details are not mentionedspecifically in each case.

Diastereomer mixtures or racemate mixtures of compounds of formula (I),in free form or in salt form, which can be obtained depending on whichstarting materials and procedures have been chosen can be separated in aknown manner into the pure diasteromers or racemates on the basis of thephysicochemical differences of the components, for example by fractionalcrystallization, distillation and/or chromatography.

Enantiomer mixtures, such as racemates, which can be obtained in asimilar manner can be resolved into the optical antipodes by knownmethods, for example by recrystallization from an optically activesolvent, by chromatography on chiral adsorbents, for examplehigh-performance liquid chromatography (HPLC) on acetyl cellulose, withthe aid of suitable microorganisms, by cleavage with specific,immobilized enzymes, via the formation of inclusion compounds, forexample using chiral crown ethers, where only one enantiomer iscomplexed, or by conversion into diastereomeric salts, for example byreacting a basic end-product racemate with an optically active acid,such as a carboxylic acid, for example camphor, tartaric or malic acid,or sulfonic acid, for example camphorsulfonic acid, and separating thediastereomer mixture which can be obtained in this manner, for exampleby fractional crystallization based on their differing solubilities, togive the diastereomers, from which the desired enantiomer can be setfree by the action of suitable agents, for example basic agents.

Pure diastereomers or enantiomers can be obtained according to theinvention not only by separating suitable isomer mixtures, but also bygenerally known methods of diastereoselective or enantioselectivesynthesis, for example by carrying out the process according to theinvention with starting materials of a suitable stereochemistry.

Compounds of formula (I) include at least one chiral centre and mayexist as compounds of formula (I*) or compounds of formula (I**):

Generally compounds of formula (I**) are more biologically active thancompounds of formula (I*). The invention includes mixtures of compounds(I*) and (I**) in any ratio e.g. in a molar ratio of 1:99 to 99:1, e.g.10:1 to 1:10, e.g. a substantially 50:50 molar ratio. In anenantiomerically (or epimerically) enriched mixture of formula (I**),the molar proportion of compound (I**) compared to the total amount ofboth enantiomers (or epimers) is for example greater than 50%, e.g. atleast 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%.Likewise, in enantiomerically (or epimerically) enriched mixture offormula (I*), the molar proportion of the compound of formula (I*)compared to the total amount of both enantiomers (or epimers) is forexample greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90,95, 96, 97, 98, or at least 99%. Enantiomerically (or epimerically)enriched mixtures of formula (I**) are preferred.

Salts of compounds of formula (I) can be prepared in a manner known perse. Thus, for example, acid addition salts of compounds of formula (I)are obtained by treatment with a suitable acid or a suitable ionexchanger reagent and salts with bases are obtained by treatment with asuitable base or with a suitable ion exchanger reagent.

Salts of compounds of formula (I) can be converted in the customarymanner into the free compounds (I), acid addition salts, for example, bytreatment with a suitable basic compound or with a suitable ionexchanger reagent and salts with bases, for example, by treatment with asuitable acid or with a suitable ion exchanger reagent.

Salts of compounds of formula (I) can be converted in a manner known perse into other salts of compounds of formula (I), acid addition salts,for example, into other acid addition salts, for example by treatment ofa salt of inorganic acid such as hydrochloride with a suitable metalsalt such as a sodium, barium or silver salt, of an acid, for examplewith silver acetate, in a suitable solvent in which an inorganic saltwhich forms, for example silver chloride, is insoluble and thusprecipitates from the reaction mixture.

Depending on the procedure or the reaction conditions, the compounds offormula (I), which have salt-forming properties, can be obtained in freeform or in the form of salts.

N-oxides can be prepared by reacting a compound of the formula (I) witha suitable oxidizing agent, for example the H₂O₂/urea adduct in thepresence of an acid anhydride, e.g. trifluoroacetic anhydride. Suchoxidations are known from the literature, for example from J. Med. Chem.1989, 32, 2561 or WO200015615.

It is advantageous to isolate or synthesize in each case thebiologically more effective isomer, for example enantiomer ordiastereomer, or isomer mixture, for example enantiomer mixture ordiastereomer mixture, if the individual components have a differentbiological activity.

The compounds of formula (I) and, where appropriate, the tautomersthereof, in each case in free form or in salt form, can, if appropriate,also be obtained in the form of hydrates and/or include other solvents,for example those which may have been used for the crystallization ofcompounds which are present in solid form.

The compounds according to the following Tables A-1 to A-100 below canbe prepared according to the methods described above. The examples whichfollow are intended to illustrate the invention and show preferredcompounds of formula (I).

Tables A-1 to A-100: Compounds of Formula (Ia)

The invention is further illustrated by making available the followingindividual compounds of formula (Ia) listed below in Tables A-1 toA-100.

Each of Tables A-1 to A-100, which follow the Table P below, makeavailable compounds of the formula (Ia) in which X₂, R² and R³ are thesubstituents defined in Table P and X₁, X₃ and R⁵ are the substituentsdefined in the relevant Table A-1 to A-100. Thus Table A-1individualises compounds of formula (Ia) wherein for each row of TableP, the X₁, X₃ and R⁵ substituents are as defined in Table A-1;similarly, Table A-2 individualises compounds of formula (Ia) whereinfor each row of Table P, the X₁, X₃ and R⁵ substituents are as definedin Table A-2; and so on for Tables A-3 to A-100. Each compound disclosedin Tables A-1 to A-100 represents a disclosure of a compound accordingto the compound of formula (I*), and a disclosure according to thecompound of formula (I**) as well as mixtures thereof.

TABLE P Substituent definitions of X₂, R² and R³ Index R² R³ X₂ 1 CH₃CF₃ N 2 CH₃ CF₂Cl N 3 CH₂CH₃ CF₃ N 4 CH₂CH₃ CF₂Cl N 5 CH₂Cl CF₃ N 6CH₂Cl CF₂Cl N 7 CH₂F CF₃ N 8 CH₂F CF₂Cl N 9 CHF₂ CF₃ N 10 CHF₂ CF₂Cl N11 CF₃ CF₃ N 12 CF₃ CF₂Cl N 13 CH₂CF₃ CF₃ N 14 CH₂CF₃ CF₂Cl N 15 CH₃ CF₃C—H 16 CH₃ CF₂Cl C—H 17 CH₂CH₃ CF₃ C—H 18 CH₂CH₃ CF₂Cl C—H 19 CH₂Cl CF₃C—H 20 CH₂Cl CF₂Cl C—H 21 CH₂F CF₃ C—H 22 CH₂F CF₂Cl C—H 23 CHF₂ CF₃ C—H24 CHF₂ CF₂Cl C—H 25 CF₃ CF₃ C—H 26 CF₃ CF₂Cl C—H 27 CH₂CF₃ CF₃ C—H 28CH₂CF₃ CF₂Cl C—H 29 CH₃ CF₃ C—Cl 30 CH₃ CF₂Cl C—Cl 31 CH₂CH₃ CF₃ C—Cl 32CH₂CH₃ CF₂Cl C—Cl 33 CH₂Cl CF₃ C—Cl 34 CH₂Cl CF₂Cl C—Cl 35 CH₂F CF₃ C—Cl36 CH₂F CF₂Cl C—Cl 37 CHF₂ CF₃ C—Cl 38 CHF₂ CF₂Cl C—Cl 39 CF₃ CF₃ C—Cl40 CF₃ CF₂Cl C—Cl 41 CH₂CF₃ CF₃ C—Cl 42 CH₂CF₃ CF₂Cl C—Cl 43 CH₃ CF₃C—Br 44 CH₃ CF₂Cl C—Br 45 CH₂CH₃ CF₃ C—Br 46 CH₂CH₃ CF₂Cl C—Br 47 CH₂ClCF₃ C—Br 48 CH₂Cl CF₂Cl C—Br 49 CH₂F CF₃ C—Br 50 CH₂F CF₂Cl C—Br 51 CHF₂CF₃ C—Br 52 CHF₂ CF₂Cl C—Br 53 CF₃ CF₃ C—Br 54 CF₃ CF₂Cl C—Br 55 CH₂CF₃CF₃ C—Br 56 CH₂CF₃ CF₂Cl C—Br 57 CH₃ CF₃ C—F 58 CH₃ CF₂Cl C—F 59 CH₂CH₃CF₃ C—F 60 CH₂CH₃ CF₂Cl C—F 61 CH₂Cl CF₃ C—F 62 CH₂Cl CF₂Cl C—F 63 CH₂FCF₃ C—F 64 CH₂F CF₂Cl C—F 65 CHF₂ CF₃ C—F 66 CHF₂ CF₂Cl C—F 67 CF₃ CF₃C—F 68 CF₃ CF₂Cl C—F 69 CH₂CF₃ CF₃ C—F 70 CH₂CF₃ CF₂Cl C—F 71 CH₃ CF₃C—CF₃ 72 CH₃ CF₂Cl C—CF₃ 73 CH₂CH₃ CF₃ C—CF₃ 74 CH₂CH₃ CF₂Cl C—CF₃ 75CH₂Cl CF₃ C—CF₃ 76 CH₂Cl CF₂Cl C—CF₃ 77 CH₂F CF₃ C—CF₃ 78 CH₂F CF₂ClC—CF₃ 79 CHF₂ CF₃ C—CF₃ 80 CHF₂ CF₂Cl C—CF₃ 81 CF₃ CF₃ C—CF₃ 82 CF₃CF₂Cl C—CF₃ 83 CH₂CF₃ CF₃ C—CF₃ 84 CH₂CF₃ CF₂Cl C—CF₃ 85 CH₂Br CF₃ N 86CH₂Br CF₂Cl N 87 CH₂Br CF₃ C—H 88 CH₂Br CF₂Cl C—H 89 CH₂Br CF₃ C—Cl 90CH₂Br CF₂Cl C—Cl 91 CH₂Br CF₃ C—Br 92 CH₂Br CF₂Cl C—Br 93 CH₂Br CF₃ C—F94 CH₂Br CF₂Cl C—F 95 CH₂Br CF₃ C—CF₃ 96 CH₂Br CF₂Cl C—CF₃Table A-1 provides 96 compounds A-1.001 to A-1.096 of formula Ia whereinX₁ is H, X₃ is H, R⁵ is CH₃ and X₂, R², R³ are as defined in table P.Table A-2 provides 96 compounds A-2.001 to A-2.096 of formula Ia whereinX₁ is H, X₃ is H, R⁵ is C₁ and X₂, R², R³ are as defined in table P.Table A-3 provides 96 compounds A-3.001 to A-3.096 of formula Ia whereinX₁ is H, X₃ is H, R⁵ is Br and X₂, R², R³ are as defined in table P.Table A-4 provides 96 compounds A-4.001 to A-4.096 of formula Ia whereinX₁ is H, X₃ is H, R⁵ is CF₃ and X₂, R², R³ are as defined in table P.Table A-5 provides 96 compounds A-5.001 to A-5.096 of formula Ia whereinX₁ is H, X₃ is Cl, R⁵ is CH₃ and X₂, R², R³ are as defined in table P.Table A-6 provides 96 compounds A-6.001 to A-6.096 of formula Ia whereinX₁ is H, X₃ is Cl, R⁵ is C₁ and X₂, R², R³ are as defined in table P.Table A-7 provides 96 compounds A-7.001 to A-7.096 of formula Ia whereinX₁ is H, X₃ is Cl, R⁵ is Br and X₂, R², R³ are as defined in table P.Table A-8 provides 96 compounds A-8.001 to A-8.096 of formula Ia whereinX₁ is H, X₃ is Cl, R⁵ is CF₃ and X₂, R², R³ are as defined in table P.Table A-9 provides 96 compounds A-9.001 to A-9.096 of formula Ia whereinX₁ is H, X₃ is Br, R⁵ is CH₃ and X₂, R², R³ are as defined in table P.Table A-10 provides 96 compounds A-10.001 to A-10.096 of formula Iawherein X₁ is H, X₃ is Br, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-11 provides 96 compounds A-11.001 to A-11.096 of formula Iawherein X₁ is H, X₃ is Br, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-12 provides 96 compounds A-12.001 to A-12.096 of formula Iawherein X₁ is H, X₃ is Br, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-13 provides 96 compounds A-13.001 to A-13.096 of formula Iawherein X₁ is H, X₃ is F, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-14 provides 96 compounds A-14.001 to A-14.096 of formula Iawherein X₁ is H, X₃ is F, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-15 provides 96 compounds A-15.001 to A-15.096 of formula Iawherein X₁ is H, X₃ is F, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-16 provides 96 compounds A-16.001 to A-16.096 of formula Iawherein X₁ is H, X₃ is F, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-17 provides 96 compounds A-17.001 to A-17.096 of formula Iawherein X₁ is H, X₃ is CF₃, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-18 provides 96 compounds A-18.001 to A-18.096 of formula Iawherein X₁ is H, X₃ is CF₃, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-19 provides 96 compounds A-19.001 to A-19.096 of formula Iawherein X₁ is H, X₃ is CF₃, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-20 provides 96 compounds A-20.001 to A-20.096 of formula Iawherein X₁ is H, X₃ is CF₃, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-21 provides 96 compounds A-21.001 to A-21.096 of formula Iawherein X₁ is Cl, X₃ is H, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-22 provides 96 compounds A-22.001 to A-22.096 of formula Iawherein X₁ is Cl, X₃ is H, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-23 provides 96 compounds A-23.001 to A-23.096 of formula Iawherein X₁ is Cl, X₃ is H, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-24 provides 96 compounds A-24.001 to A-24.096 of formula Iawherein X₁ is Cl, X₃ is H, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-25 provides 96 compounds A-25.001 to A-25.096 of formula Iawherein X₁ is Cl, X₃ is Cl, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-26 provides 96 compounds A-26.001 to A-26.096 of formula Iawherein X₁ is Cl, X₃ is Cl, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-27 provides 96 compounds A-27.001 to A-27.096 of formula Iawherein X₁ is Cl, X₃ is Cl, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-28 provides 96 compounds A-28.001 to A-28.096 of formula Iawherein X₁ is Cl, X₃ is Cl, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-29 provides 96 compounds A-29.001 to A-29.096 of formula Iawherein X₁ is Cl, X₃ is Br, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-30 provides 96 compounds A-30.001 to A-30.096 of formula Iawherein X₁ is Cl, X₃ is Br, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-31 provides 96 compounds A-31.001 to A-31.096 of formula Iawherein X₁ is Cl, X₃ is Br, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-32 provides 96 compounds A-32.001 to A-32.096 of formula Iawherein X₁ is Cl, X₃ is Br, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-33 provides 96 compounds A-33.001 to A-33.096 of formula Iawherein X₁ is Cl, X₃ is F, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-34 provides 96 compounds A-34.001 to A-34.096 of formula Iawherein X₁ is Cl, X₃ is F, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-35 provides 96 compounds A-35.001 to A-35.096 of formula Iawherein X₁ is Cl, X₃ is F, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-36 provides 96 compounds A-36.001 to A-36.096 of formula Iawherein X₁ is Cl, X₃ is F, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-37 provides 96 compounds A-37.001 to A-37.096 of formula Iawherein X₁ is Cl, X₃ is CF₃, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-38 provides 96 compounds A-38.001 to A-38.096 of formula Iawherein X₁ is Cl, X₃ is CF₃, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-39 provides 96 compounds A-39.001 to A-39.096 of formula Iawherein X₁ is Cl, X₃ is CF₃, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-40 provides 96 compounds A-40.001 to A-40.096 of formula Iawherein X₁ is Cl, X₃ is CF₃, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-41 provides 96 compounds A-41.001 to A-41.096 of formula Iawherein X₁ is Br, X₃ is H, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-42 provides 96 compounds A-42.001 to A-42.096 of formula Iawherein X₁ is Br, X₃ is H, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-43 provides 96 compounds A-43.001 to A-43.096 of formula Iawherein X₁ is Br, X₃ is H, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-44 provides 96 compounds A-44.001 to A-44.096 of formula Iawherein X₁ is Br, X₃ is H, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-45 provides 96 compounds A-45.001 to A-45.096 of formula Iawherein X₁ is Br, X₃ is Cl, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-46 provides 96 compounds A-46.001 to A-46.096 of formula Iawherein X₁ is Br, X₃ is Cl, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-47 provides 96 compounds A-47.001 to A-47.096 of formula Iawherein X₁ is Br, X₃ is Cl, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-48 provides 96 compounds A-48.001 to A-48.096 of formula Iawherein X₁ is Br, X₃ is Cl, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-49 provides 96 compounds A-49.001 to A-49.096 of formula Iawherein X₁ is Br, X₃ is Br, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-50 provides 96 compounds A-50.001 to A-50.096 of formula Iawherein X₁ is Br, X₃ is Br, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-51 provides 96 compounds A-51.001 to A-51.096 of formula Iawherein X₁ is Br, X₃ is Br, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-52 provides 96 compounds A-52.001 to A-52.096 of formula Iawherein X₁ is Br, X₃ is Br, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-53 provides 96 compounds A-53.001 to A-53.096 of formula Iawherein X₁ is Br, X₃ is F, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-54 provides 96 compounds A-54.001 to A-54.096 of formula Iawherein X₁ is Br, X₃ is F, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-55 provides 96 compounds A-55.001 to A-55.096 of formula Iawherein X₁ is Br, X₃ is F, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-56 provides 96 compounds A-56.001 to A-56.096 of formula Iawherein X₁ is Br, X₃ is F, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-57 provides 96 compounds A-57.001 to A-57.096 of formula Iawherein X₁ is Br, X₃ is CF₃, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-58 provides 96 compounds A-58.001 to A-58.096 of formula Iawherein X₁ is Br, X₃ is CF₃, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-59 provides 96 compounds A-59.001 to A-59.096 of formula Iawherein X₁ is Br, X₃ is CF₃, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-60 provides 96 compounds A-60.001 to A-60.096 of formula Iawherein X₁ is Br, X₃ is CF₃, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-61 provides 96 compounds A-61.001 to A-61.096 of formula Iawherein X₁ is F, X₃ is H, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-62 provides 96 compounds A-62.001 to A-62.096 of formula Iawherein X₁ is F, X₃ is H, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-63 provides 96 compounds A-63.001 to A-63.096 of formula Iawherein X₁ is F, X₃ is H, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-64 provides 96 compounds A-64.001 to A-64.096 of formula Iawherein X₁ is F, X₃ is H, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-65 provides 96 compounds A-65.001 to A-65.096 of formula Iawherein X₁ is F, X₃ is Cl, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-66 provides 96 compounds A-66.001 to A-66.096 of formula Iawherein X₁ is F, X₃ is Cl, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-67 provides 96 compounds A-67.001 to A-67.096 of formula Iawherein X₁ is F, X₃ is Cl, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-68 provides 96 compounds A-68.001 to A-68.096 of formula Iawherein X₁ is F, X₃ is Cl, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-69 provides 96 compounds A-69.001 to A-69.096 of formula Iawherein X₁ is F, X₃ is Br, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-70 provides 96 compounds A-70.001 to A-70.096 of formula Iawherein X₁ is F, X₃ is Br, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-71 provides 96 compounds A-71.001 to A-71.096 of formula Iawherein X₁ is F, X₃ is Br, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-72 provides 96 compounds A-72.001 to A-72.096 of formula Iawherein X₁ is F, X₃ is Br, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-73 provides 96 compounds A-73.001 to A-73.096 of formula Iawherein X₁ is F, X₃ is F, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-74 provides 96 compounds A-74.001 to A-74.096 of formula Iawherein X₁ is F, X₃ is F, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-75 provides 96 compounds A-75.001 to A-75.096 of formula Iawherein X₁ is F, X₃ is F, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-76 provides 96 compounds A-76.001 to A-76.096 of formula Iawherein X₁ is F, X₃ is F, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-77 provides 96 compounds A-77.001 to A-77.096 of formula Iawherein X₁ is F, X₃ is CF₃, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-78 provides 96 compounds A-78.001 to A-78.096 of formula Iawherein X₁ is F, X₃ is CF₃, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-79 provides 96 compounds A-79.001 to A-79.096 of formula Iawherein X₁ is F, X₃ is CF₃, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-80 provides 96 compounds A-80.001 to A-80.096 of formula Iawherein X₁ is F, X₃ is CF₃, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-81 provides 96 compounds A-81.001 to A-81.096 of formula Iawherein X₁ is CF₃, X₃ is H, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-82 provides 96 compounds A-82.001 to A-82.096 of formula Iawherein X₁ is CF₃, X₃ is H, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-83 provides 96 compounds A-83.001 to A-83.096 of formula Iawherein X₁ is CF₃, X₃ is H, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-84 provides 96 compounds A-84.001 to A-84.096 of formula Iawherein X₁ is CF₃, X₃ is H, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-85 provides 96 compounds A-85.001 to A-85.096 of formula Iawherein X₁ is CF₃, X₃ is Cl, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-86 provides 96 compounds A-86.001 to A-86.096 of formula Iawherein X₁ is CF₃, X₃ is Cl, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-87 provides 96 compounds A-87.001 to A-87.096 of formula Iawherein X₁ is CF₃, X₃ is Cl, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-88 provides 96 compounds A-88.001 to A-88.096 of formula Iawherein X₁ is CF₃, X₃ is Cl, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-89 provides 96 compounds A-89.001 to A-89.096 of formula Iawherein X₁ is CF₃, X₃ is Br, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-90 provides 96 compounds A-90.001 to A-90.096 of formula Iawherein X₁ is CF₃, X₃ is Br, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-91 provides 96 compounds A-91.001 to A-91.096 of formula Iawherein X₁ is CF₃, X₃ is Br, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-92 provides 96 compounds A-92.001 to A-92.096 of formula Iawherein X₁ is CF₃, X₃ is Br, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-93 provides 96 compounds A-93.001 to A-93.096 of formula Iawherein X₁ is CF₃, X₃ is F, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-94 provides 96 compounds A-94.001 to A-94.096 of formula Iawherein X₁ is CF₃, X₃ is F, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-95 provides 96 compounds A-95.001 to A-95.096 of formula Iawherein X₁ is CF₃, X₃ is F, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-96 provides 96 compounds A-96.001 to A-96.096 of formula Iawherein X₁ is CF₃, X₃ is F, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.Table A-97 provides 96 compounds A-97.001 to A-97.096 of formula Iawherein X₁ is CF₃, X₃ is CF₃, R⁵ is CH₃ and X₂, R², R³ are as defined intable P.Table A-98 provides 96 compounds A-98.001 to A-98.096 of formula Iawherein X₁ is CF₃, X₃ is CF₃, R⁵ is Cl and X₂, R², R³ are as defined intable P.Table A-99 provides 96 compounds A-99.001 to A-99.096 of formula Iawherein X₁ is CF₃, X₃ is CF₃, R⁵ is Br and X₂, R², R³ are as defined intable P.Table A-100 provides 96 compounds A-100.001 to A-100.096 of formula Iawherein X₁ is CF₃, X₃ is CF₃, R⁵ is CF₃ and X₂, R², R³ are as defined intable P.

Examples of compounds of formula (Int-I) made available are those whereX^(B) is bromo, chloro, iodo, cyano, formyl, CH═NOH or acetyl, A², A³and A⁴ are each CH, R¹ is hydrogen, A¹ is CR⁵ and R⁶ is hydrogen.Alternatively, X^(B) is bromo, chloro, iodo, cyano, formyl, CH═NOH oracetyl, A², A³ and A⁴ are each CH, R¹ is hydrogen, A¹ is CR⁵ and R⁶ isS(O)₂R², wherein R² and R⁵ are the substituents defined in Table Qbelow. Each of Tables B-1 to B-7, which follow the Table Q below, makeavailable compounds of the formula (Int-I) in which R² and R⁵ are thesubstituents defined in Table Q and X^(B) is as defined in the relevantTable B-1 to B-7.

TABLE Q Index R² R⁵ 1 CH₃ CH₃ 2 CH₃ Cl 3 CH₃ Br 4 CH₃ CF₃ 5 CH₂CH₃ CH₃ 6CH₂CH₃ Cl 7 CH₂CH₃ Br 8 CH₂CH₃ CF₃ 9 CH₂Cl CH₃ 10 CH₂Cl Cl 11 CH₂Cl Br12 CH₂Cl CF₃ 13 CH₂F CH₃ 14 CH₂F Cl 15 CH₂F Br 16 CH₂F CF₃ 17 CHF₂ CH₃18 CHF₂ Cl 19 CHF₂ Br 20 CHF₂ CF₃ 21 CF₃ CH₃ 22 CF₃ Cl 23 CF₃ Br 24 CF₃CF₃ 25 CH₂CF₃ CH₃ 26 CH₂CF₃ Cl 27 CH₂CF₃ Br 28 CH₂CF₃ CF₃ 29 CH₂Br CH₃30 CH₂Br Cl 31 CH₂Br Br 32 CH₂Br CF₃Table B-1 provides 32 compounds B-1.01 to B-1.32 of formula (Int-I)wherein X^(B) is bromo and R² and R⁵ are as defined in Table Q.Table B-2 provides 32 compounds B-2.01 to B-2.32 of formula (Int-I)wherein X^(B) is chloro and R² and R⁵ are as defined in Table Q.Table B-3 provides 32 compounds B-3.01 to B-3.32 of formula (Int-I)wherein X^(B) is iodo and R² and R⁵ are as defined in Table Q.Table B-4 provides 32 compounds B-4.01 to B-4.32 of formula (Int-I)wherein X^(B) is cyano and R² and R⁵ are as defined in Table Q.Table B-5 provides 32 compounds B-5.01 to B-5.32 of formula (Int-I)wherein X^(B) is formyl and R² and R⁵ are as defined in Table Q.Table B-6 provides 32 compounds B-6.01 to B-6.32 of formula (Int-I)wherein X^(B) is CH═NOH and R² and R⁵ are as defined in Table Q.Table B-7 provides 32 compounds B-7.01 to B-7.32 of formula (Int-I)wherein X^(B) is acetyl and R² and R⁵ are as defined in Table Q.Examples of compounds of formula (Int-II) made available are those whereX^(C) is CH₂Cl, CH₂Br, CH═C(CF₃)(3-chloro-5-trifluoromethyl-phenyl),CH═C(CF₃)(3-bromo-5-trifluoromethyl-phenyl),CH═C(CF₃)(3,5-dichloro-4-fluoro-phenyl),CH═C(CF₃)(3,4,5-trichloro-phenyl),CH₂C(OH)(CF₃)(3-chloro-5-trifluoromethyl-phenyl),CH₂C(OH)(CF₃)(3-bromo-5-trifluoromethyl-phenyl),CH₂C(OH)(CF₃)(3,5-dichloro-4-fluoro-phenyl) orCH₂C(OH)(CF₃)(3,4,5-trichloro-phenyl), A², A³ and A⁴ are each CH, R¹ ishydrogen, A¹ is CR⁵ and R⁶ is hydrogen. Alternatively, X^(C) is CH₂Cl,CH₂Br, CH═C(CF₃)(3-chloro-5-trifluoromethyl-phenyl),CH═C(CF₃)(3-bromo-5-trifluoromethyl-phenyl),CH═C(CF₃)(3,5-dichloro-4-fluoro-phenyl),CH═C(CF₃)(3,4,5-trichloro-phenyl),CH₂C(OH)(CF₃)(3-chloro-5-trifluoromethyl-phenyl),CH₂C(OH)(CF₃)(3-bromo-5-trifluoromethyl-phenyl),CH₂C(OH)(CF₃)(3,5-dichloro-4-fluoro-phenyl) orCH₂C(OH)(CF₃)(3,4,5-trichloro-phenyl), A², A³ and A⁴ are each CH, R¹ ishydrogen, A¹ is CR⁵ and R⁶ is S(O)₂R², wherein R² and R⁵ correspond tothe substituents R² and R⁵ as defined in Table Q above. Each of TablesC-1 to C-10, which follow below, make available compounds of the formula(Int-II) in which R² and R⁵ are the substituents defined in Table Q andX^(C) is as defined in the relevant Table C-1 to C-10.Table C-1 provides 32 compounds C-1.01 to C-1.32 of formula (Int-II)wherein X^(C) is CH₂Cl and R² and R⁵ are as defined in Table Q.Table C-2 provides 32 compounds C-2.01 to C-2.32 of formula (Int-II)wherein X^(C) is CH₂Br and R² and R⁵ are as defined in Table Q.Table C-3 provides 32 compounds C-3.01 to C-3.32 of formula (Int-II)wherein X^(C) is CH═C(CF₃)(3-chloro-5-trifluoromethyl-phenyl) and R² andR⁵ are as defined in Table Q.Table C-4 provides 32 compounds C-4.01 to C-4.32 of formula (Int-II)wherein X^(C) is CH═C(CF₃)(3-bromo-5-trifluoromethyl-phenyl) and R² andR⁵ are as defined in Table Q.Table C-5 provides 32 compounds C-5.01 to C-5.32 of formula (Int-II)wherein X^(C) is CH═C(CF₃)(3,5-dichloro-4-fluoro-phenyl) and R² and R⁵are as defined in Table Q.Table C-6 provides 32 compounds C-6.01 to C-6.32 of formula (Int-II)wherein X^(C) is CH═C(CF₃)(3,4,5-trichloro-phenyl) and R² and R⁵ are asdefined in Table Q.Table C-7 provides 32 compounds C-7.01 to C-7.32 of formula (Int-II)wherein X^(C) is CH₂C(OH)(CF₃)(3-chloro-5-trifluoromethyl-phenyl) and R²and R⁵ are as defined in Table Q.Table C-8 provides 32 compounds C-8.01 to C-8.32 of formula (Int-II)wherein X^(C) is CH₂C(OH)(CF₃)(3-bromo-5-trifluoromethyl-phenyl) and R²and R⁵ are as defined in Table Q.Table C-9 provides 32 compounds C-9.01 to C-9.32 of formula (Int-II)wherein X^(C) is CH₂C(OH)(CF₃)(3,5-dichloro-4-fluoro-phenyl) and R² andR⁵ are as defined in Table Q.Table C-10 provides 32 compounds C-10.01 to C-10.32 of formula (Int-II)wherein X^(C) is CH₂C(OH)(CF₃)(3,4,5-trichloro-phenyl) and R² and R⁵ areas defined in Table Q.

The compounds of formula (I) according to the invention are preventivelyand/or curatively valuable active ingredients in the field of pestcontrol, even at low rates of application, which have a very favorablebiocidal spectrum and are well tolerated by warm-blooded species, fishand plants. The active ingredients according to the invention actagainst all or individual developmental stages of normally sensitive,but also resistant, animal pests, such as insects or representatives ofthe order Acarina. The insecticidal or acaricidal activity of the activeingredients according to the invention can manifest itself directly, i.e. in destruction of the pests, which takes place either immediately oronly after some time has elapsed, for example during ecdysis, orindirectly, for example in a reduced oviposition and/or hatching rate.

Examples of the abovementioned animal pests are:from the order Acarina, for example,Acalitus spp, Aculus spp, Acaricalus spp, Aceria spp, Acarus siro,Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobiaspp, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae,Dermatophagoides spp, Eotetranychus spp, Eriophyes spp., Hemitarsonemusspp, Hyalomma spp., Ixodes spp., Olygonychus spp, Ornithodoros spp.,Polyphagotarsone latus, Panonychus spp., Phyllocoptruta oleivora,Phytonemus spp, Polyphagotarsonemus spp, Psoroptes spp., Rhipicephalusspp., Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp,Tarsonemus spp. and Tetranychus spp.;from the order Anoplura, for example,

Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. andPhylloxera spp.;

from the order Coleoptera, for example,Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp.,Aphodius spp, Astylus atromaculatus, Ataenius spp, Atomaria linearis,Chaetocnema tibialis, Cerotoma spp, Conoderus spp, Cosmopolites spp.,Cotinis nitida, Curculio spp., Cyclocephala spp, Dermestes spp.,Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp.,Heteronychus arator, Hypothenemus hampei, Lagria vilosa, LeptinotarsadecemLineata, Lissorhoptrus spp., Liogenys spp, Maecolaspis spp,Maladera castanea, Megascelis spp, Melighetes aeneus, Melolontha spp.,Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophagaspp, Phlyctinus spp., Popillia spp., Psylliodes spp., Rhyssomatusaubtilis, Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotrogaspp., Somaticus spp, Sphenophorus spp, Sternechus subsignatus, Tenebriospp., Tribolium spp. and Trogoderma spp.;from the order Diptera, for example,Aedes spp., Anopheles spp, Antherigona soccata, Bactrocea oleae, Bibiohortulanus, Bradysia spp, Calliphora erythrocephala, Ceratitis spp.,Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp,Drosophila melanogaster, Fannia spp., Gastrophilus spp., Geomyzatripunctata, Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyzaspp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp.,Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp.,Rhagoletis spp, Rivelia quadrifasciata, Scatella spp, Sciara spp.,Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.;from the order Hemiptera, for example,Acanthocoris scabrator, Acrosternum spp, Adelphocoris lineolatus,Amblypelta nitida, Bathycoelia thalassina, Blissus spp, Cimex spp.,Clavigralla tomentosicollis, Creontiades spp, Distantiella theobroma,Dichelops furcatus, Dysdercus spp., Edessa spp, Euchistus spp., Eurydemapulchrum, Eurygaster spp., Halyomorpha halys, Horcias nobilellus,Leptocorisa spp., Lygus spp, Margarodes spp, Murgantia histrionic,Neomegalotomus spp, Nesidiocoris tenuis, Nezara spp., Nysius simulans,Oebalus insularis, Piesma spp., Piezodorus spp, Rhodnius spp.,Sahlbergella singularis, Scaptocoris castanea, Scotinophara spp.,Thyanta spp, Triatoma spp., Vatiga illudens; Acyrthosium pisum, Adalgesspp, Agalliana ensigera, Agonoscena targionii, Aleurodicus spp,Aleurocanthus spp, Aleurolobus barodensis, Aleurothrixus floccosus,Aleyrodes brassicae, Amarasca biguttula, Amritodus atkinsoni, Aonidiellaspp., Aphididae, Aphis spp., Aspidiotus spp., Aulacorthum solani,Bactericera cockerelli, Bemisia spp, Brachycaudus spp, Brevicorynebrassicae, Cacopsylla spp, Cavariella aegopodii Scop., Ceroplaster spp.,Chrysomphalus aonidium, Chrysomphalus dictyospermi, Cicadella spp,Cofana spectra, Cryptomyzus spp, Cicadulina spp, Coccus hesperidum,Dalbulus maidis, Dialeurodes spp, Diaphorina citri, Diuraphis noxia,Dysaphis spp, Empoasca spp., Eriosoma larigerum, Erythroneura spp.,Gascardia spp., Glycaspis brimblecombei, Hyadaphis pseudobrassicae,Hyalopterus spp, Hyperomyzus pallidus, Idioscopus clypealis, Jacobiascalybica, Laodelphax spp., Lecanium corni, Lepidosaphes spp., Lopaphiserysimi, Lyogenys maidis, Macrosiphum spp., Mahanarva spp, Metcalfapruinosa, Metopolophium dirhodum, Myndus crudus, Myzus spp.,Neotoxoptera sp, Nephotettix spp., Nilaparvata spp., Nippolachnus piriMats, Odonaspis ruthae, Oregma lanigera Zehnter, Parabemisia myricae,Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Peregrinusmaidis, Perkinsiella spp, Phorodon humuli, Phylloxera spp, Planococcusspp., Pseudaulacaspis spp., Pseudococcus spp., Pseudatomoscelisseriatus, Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp.,Quesada gigas, Recilia dorsalis, Rhopalosiphum spp., Saissetia spp.,Scaphoideus spp., Schizaphis spp., Sitobion spp., Sogatella furcifera,Spissistilus festinus, Tarophagus Proserpina, Toxoptera spp,Trialeurodes spp, Tridiscus sporoboli, Trionymus spp, Trioza erytreae,Unaspis citri, Zygina flammigera, Zyginidia scutellaris;from the order Hymenoptera, for example,Acromyrmex, Arge spp, Atta spp., Cephus spp., Diprion spp., Diprionidae,Gilpinia polytoma, Hoplo-campa spp., Lasius spp., Monomorium pharaonis,Neodiprion spp., Pogonomyrmex spp, Slenopsis invicta, Solenopsis spp.and Vespa spp.;from the order Isoptera, for example,Coptotermes spp, Corniternes cumulans, Incisitermes spp, Macrotermesspp, Mastotermes spp, Microtermes spp, Reticulitermes spp.; Solenopsisgeminatefrom the order Lepidoptera, for example,Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabamaargillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp.,Argyresthia spp, Argyrotaenia spp., Autographa spp., Bucculatrixthurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis,Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysiaambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp.,Coleophora spp., Colias lesbia, Cosmophila flava, Crambus spp,Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis,Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea,Earias spp., Eldana saccharina, Ephestia spp., Epinotia spp, Estigmeneacrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella,Euproctis spp., Euxoa spp., Feltia jaculiferia, Grapholita spp., Hedyanubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp,Hyphantria cunea, Keiferia lycopersicella, Lasmopalpus lignosellus,Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Loxostegebifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestrabrassicae, Manduca sexta, Mythimna spp, Noctua spp, Operophtera spp.,Orniodes indica, Ostrinia nubilalis, Pammene spp., Pandemis spp.,Panolis flammea, Papaipema nebris, Pectinophora gossypi-ela,Perileucoptera coffeella, Pseudaletia unipuncta, Phthorimaeaoperculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp.,Pseudoplusia spp, Rachiplusia nu, Richia albicosta, Scirpophaga spp.,Sesamia spp., Sparganothis spp., Spodoptera spp., Sylepta derogate,Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tutaabsoluta, and Yponomeuta spp.; from the order Mallophaga, for example,Damalinea spp. and Trichodectes spp.;from the order Orthoptera, for example,Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae,Locusta spp., Neocurtilla hexadactyla, Periplaneta spp., Scapteriscusspp, and Schistocerca spp.;from the order Psocoptera, for example,

Liposcelis spp.;

from the order Siphonaptera, for example,Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis;from the order Thysanoptera, for example,Calliothrips phaseoli, Frankliniella spp., Heliothrips spp,Hercinothrips spp., Parthenothrips spp, Scirtothrips aurantii,Sericothrips variabilis, Taeniothrips spp., Thrips spp;from the order Thysanura, for example, Lepisma saccharina.

The active ingredients according to the invention can be used forcontrolling, i. e. containing or destroying, pests of the abovementionedtype which occur in particular on plants, especially on useful plantsand ornamentals in agriculture, in horticulture and in forests, or onorgans, such as fruits, flowers, foliage, stalks, tubers or roots, ofsuch plants, and in some cases even plant organs which are formed at alater point in time remain protected against these pests.

Suitable target crops are, in particular, cereals, such as wheat,barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodderbeet; fruit, for example pomaceous fruit, stone fruit or soft fruit,such as apples, pears, plums, peaches, almonds, cherries or berries, forexample strawberries, raspberries or blackberries; leguminous crops,such as beans, lentils, peas or soya; oil crops, such as oilseed rape,mustard, poppies, olives, sunflowers, coconut, castor, cocoa or groundnuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants,such as cotton, flax, hemp or jute; citrus fruit, such as oranges,lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce,asparagus, cabbages, carrots, onions, tomatoes, potatoes or bellpeppers; Lauraceae, such as avocado, Cinnamonium or camphor; and alsotobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines,hops, the plantain family and latex plants.

The compositions and/or methods of the present invention may be alsoused on any ornamental and/or vegetable crops, including flowers,shrubs, broad-leaved trees and evergreens.

For example the invention may be used on any of the following ornamentalspecies: Ageratum spp., Alonsoa spp., Anemone spp., Anisodonteacapsenisis, Anthemis spp., Antirrhinum spp., Aster spp., Begonia spp.(e.g. B. elatior, B. semperflorens, B. tubéreux), Bougainvillea spp.,Brachycome spp., Brassica spp. (ornamental), Calceolaria spp., Capsicumannuum, Catharanthus roseus, Canna spp., Centaurea spp., Chrysanthemumspp., Cineraria spp. (C. maritime), Coreopsis spp., Crassula coccinea,Cuphea ignea, Dahlia spp., Delphinium spp., Dicentra spectabilis,Dorotheantus spp., Eustoma grandiflorum, Forsythia spp., Fuchsia spp.,Geranium gnaphalium, Gerbera spp., Gomphrena globosa, Heliotropium spp.,Helianthus spp., Hibiscus spp., Hortensia spp., Hydrangea spp.,Hypoestes phyllostachya, Impatiens spp. (I. Walleriana), Iresines spp.,Kalanchoe spp., Lantana camara, Lavatera trimestris, Leonotis leonurus,Lilium spp., Mesembryanthemum spp., Mimulus spp., Monarda spp., Nemesiaspp., Tagetes spp., Dianthus spp. (carnation), Canna spp., Oxalis spp.,Bellis spp., Pelargonium spp. (P. peltatum, P. Zonale), Viola spp.(pansy), Petunia spp., Phlox spp., Plecthranthus spp., Poinsettia spp.,Parthenocissus spp. (P. quinquefolia, P. tricuspidata), Primula spp.,Ranunculus spp., Rhododendron spp., Rosa spp. (rose), Rudbeckia spp.,Saintpaulia spp., Salvia spp., Scaevola aemola, Schizanthuswisetonensis, Sedum spp., Solanum spp., Surfinia spp., Tagetes spp.,Nicotinia spp., Verbena spp., Zinnia spp. and other bedding plants.

For example the invention may be used on any of the following vegetablespecies: Allium spp. (A. sativum, A. cepa, A. oschaninii, A. Porrum, A.ascalonicum, A. fistulosum), Anthriscus cerefolium, Apium graveolus,Asparagus officinalis, Beta vulgarus, Brassica spp. (B. Oleracea, B.Pekinensis, B. rapa), Capsicum annuum, Cicer arietinum, Cichoriumendivia, Cichorum spp. (C. intybus, C. endivia), Citrillus lanatus,Cucumis spp. (C. sativus, C. melo), Cucurbita spp. (C. pepo, C. maxima),Cyanara spp. (C. scolymus, C. cardunculus), Daucus carota, Foeniculumvulgare, Hypericum spp., Lactuca sativa, Lycopersicon spp. (L.esculentum, L. lycopersicum), Mentha spp., Ocimum basilicum,Petroselinum crispum, Phaseolus spp. (P. vulgaris, P. coccineus), Pisumsativum, Raphanus sativus, Rheum rhaponticum, Rosemarinus spp., Salviaspp., Scorzonera hispanica, Solanum melongena, Spinacea oleracea,Valerianella spp. (V. locusta, V. eriocarpa) and Vicia faba.

Preferred ornamental species include African violet, Begonia, Dahlia,Gerbera, Hydrangea, Verbena, Rosa, Kalanchoe, Poinsettia, Aster,Centaurea, Coreopsis, Delphinium, Monarda, Phlox, Rudbeckia, Sedum,Petunia, Viola, Impatiens, Geranium, Chrysanthemum, Ranunculus, Fuchsia,Salvia, Hortensia, rosemary, sage, St. Johnswort, mint, sweet pepper,tomato and cucumber.

The active ingredients according to the invention are especiallysuitable for controlling Aphis craccivora, Diabrotica balteata,Heliothis virescens, Myzus persicae, Plutella xylostella and Spodopteralittoralis in cotton, vegetable, maize, rice and soya crops. The activeingredients according to the invention are further especially suitablefor controlling Mamestra (preferably in vegetables), Cydia pomonella(preferably in apples), Empoasca (preferably in vegetables, vineyards),Leptinotarsa (preferably in potatos) and Chilo supressalis (preferablyin rice).

In a further aspect, the invention may also relate to a method ofcontrolling damage to plant and parts thereof by plant parasiticnematodes (Endoparasitic-, Semiendoparasitic- and Ectoparasiticnematodes), especially plant parasitic nematodes such as root knotnematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogynejavanica, Meloidogyne arenaria and other Meloidogyne species;cyst-forming nematodes, Globodera rostochiensis and other Globoderaspecies; Heterodera avenae, Heterodera glycines, Heterodera schachtii,Heterodera trifolii, and other Heterodera species; Seed gall nematodes,Anguina species; Stem and foliar nematodes, Aphelenchoides species;Sting nematodes, Belonolaimus longicaudatus and other Belonolaimusspecies; Pine nematodes, Bursaphelenchus xylophilus and otherBursaphelenchus species; Ring nematodes, Criconema species, Criconemellaspecies, Criconemoides species, Mesocriconema species; Stem and bulbnematodes, Ditylenchus destructor, Ditylenchus dipsaci and otherDitylenchus species; Awl nematodes, Dolichodorus species; Spiralnematodes, Heliocotylenchus multicinctus and other Helicotylenchusspecies; Sheath and sheathoid nematodes, Hemicycliophora species andHemicriconemoides species; Hirshmanniella species; Lance nematodes,Hoploaimus species; false rootknot nematodes, Nacobbus species; Needlenematodes, Longidorus elongatus and other Longidorus species; Pinnematodes, Pratylenchus species; Lesion nematodes, Pratylenchusneglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchusgoodeyi and other Pratylenchus species; Burrowing nematodes, Radopholussimilis and other Radopholus species; Reniform nematodes, Rotylenchusrobustus, Rotylenchus reniformis and other Rotylenchus species;Scutellonema species; Stubby root nematodes, Trichodorus primitivus andother Trichodorus species, Paratrichodorus species; Stunt nematodes,Tylenchorhynchus claytoni, Tylenchorhynchus dubius and otherTylenchorhynchus species; Citrus nematodes, Tylenchulus species; Daggernematodes, Xiphinema species; and other plant parasitic nematodespecies, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp.,Melinius spp., Punctodera spp., and Quinisulcius spp.

The compounds of the invention may also have activity against themolluscs. Examples of which include, for example, Ampullariidae; Arion(A. ater, A. circumscriptus, A. hortensis, A. rufus); Bradybaenidae(Bradybaena fruticum); Cepaea (C. hortensis, C. Nemoralis); ochlodina;Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum);Discus (D. rotundatus); Euomphalia; Galba (G. trunculata); Helicelia (H.itala, H. obvia); Helicidae Helicigona arbustorum); Helicodiscus; Helix(H. aperta); Limax (L. cinereoniger, L. flavus, L. marginatus, L.maximus, L. tenellus); Lymnaea; Milax (M. gagates, M. marginatus, M.sowerbyi); Opeas; Pomacea (P. canaticulata); Vallonia and Zanitoides.

Crops of useful plants in which the composition according to theinvention can be used include perennial and annual crops, such as berryplants for example blackberries, blueberries, cranberries, raspberriesand strawberries; cereals for example barley, maize (corn), millet,oats, rice, rye, sorghum triticale and wheat; fibre plants for examplecotton, flax, hemp, jute and sisal; field crops for example sugar andfodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugarcane, sunflower, tea and tobacco; fruit trees for example apple,apricot, avocado, banana, cherry, citrus, nectarine, peach, pear andplum; grasses for example Bermuda grass, bluegrass, bentgrass, centipedegrass, fescue, ryegrass, St. Augustine grass and Zoysia grass; herbssuch as basil, borage, chives, coriander, lavender, lovage, mint,oregano, parsley, rosemary, sage and thyme; legumes for example beans,lentils, peas and soya beans; nuts for example almond, cashew, groundnut, hazelnut, peanut, pecan, pistachio and walnut; palms for exampleoil palm; ornamentals for example flowers, shrubs and trees; othertrees, for example cacao, coconut, olive and rubber; vegetables forexample asparagus, aubergine, broccoli, cabbage, carrot, cucumber,garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin,rhubarb, spinach and tomato; and vines for example grapes.

Crops are to be understood as being those which are naturally occurring,obtained by conventional methods of breeding, or obtained by geneticengineering. They include crops which contain so-called output traits(e.g. improved storage stability, higher nutritional value and improvedflavour).

Crops are to be understood as also including those crops which have beenrendered tolerant to herbicides like bromoxynil or classes of herbicidessuch as ALS-, EPSPS-, GS-, HPPD- and PPO-inhibitors. An example of acrop that has been rendered tolerant to imidazolinones, e.g. imazamox,by conventional methods of breeding is Clearfield® summer canola.Examples of crops that have been rendered tolerant to herbicides bygenetic engineering methods include e.g. glyphosate- andglufosinate-resistant maize varieties commercially available under thetrade names RoundupReady®, Herculex I® and LibertyLink®.

Crops are also to be understood as being those which naturally are orhave been rendered resistant to harmful insects. This includes plantstransformed by the use of recombinant DNA techniques, for example, to becapable of synthesising one or more selectively acting toxins, such asare known, for example, from toxin-producing bacteria. Examples oftoxins which can be expressed include 8-endotoxins, vegetativeinsecticidal proteins (Vip), insecticidal proteins of bacteriacolonising nematodes, and toxins produced by scorpions, arachnids, waspsand fungi.

An example of a crop that has been modified to express the Bacillusthuringiensis toxin is the Bt maize KnockOut® (Syngenta Seeds). Anexample of a crop comprising more than one gene that codes forinsecticidal resistance and thus expresses more than one toxin isVipCot® (Syngenta Seeds). Crops or seed material thereof can also beresistant to multiple types of pests (so-called stacked transgenicevents when created by genetic modification). For example, a plant canhave the ability to express an insecticidal protein while at the sametime being herbicide tolerant, for example Herculex I® (DowAgroSciences, Pioneer Hi-Bred International).

Further areas of use of the compositions according to the invention arethe protection of stored goods and store rooms and the protection of rawmaterials, such as wood, textiles, floor coverings or buildings, andalso in the hygiene sector, especially the protection of humans,domestic animals and productive livestock against pests of the mentionedtype.

The present invention also provides a method for controlling pests (suchas mosquitoes and other disease vectors; see alsohttp://www.who.int/malaria/vector_control/irs/en/). In one embodiment,the method for controlling pests comprises applying the compositions ofthe invention to the target pests, to their locus or to a surface orsubstrate by brushing, rolling, spraying, spreading or dipping. By wayof example, an IRS (indoor residual spraying) application of a surfacesuch as a wall, ceiling or floor surface is contemplated by the methodof the invention. In another embodiment, it is contemplated to applysuch compositions to a substrate such as non-woven or a fabric materialin the form of (or which can be used in the manufacture of) netting,clothing, bedding, curtains and tents. A further object of the inventionis therefore a substrate selected from nonwoven and fabric materialcomprising a composition which contains a compound of formula (I).

In one embodiment, the method for controlling such pests comprisesapplying a pesticidally effective amount of the compositions of theinvention to the target pests, to their locus, or to a surface orsubstrate so as to provide effective residual pesticidal activity on thesurface or substrate. Such application may be made by brushing, rolling,spraying, spreading or dipping the pesticidal composition of theinvention. By way of example, an IRS application of a surface such as awall, ceiling or floor surface is contemplated by the method of theinvention so as to provide effective residual pesticidal activity on thesurface. In another embodiment, it is contemplated to apply suchcompositions for residual control of pests on a substrate such as afabric material in the form of (or which can be used in the manufactureof) netting, clothing, bedding, curtains and tents.

Substrates including non-woven, fabrics or netting to be treated may bemade of natural fibres such as cotton, raffia, jute, flax, sisal,hessian, or wool, or synthetic fibres such as polyamide, polyester,polypropylene, polyacrylonitrile or the like. The polyesters areparticularly suitable. The methods of textile treatment are known, e.g.WO 2008/151984, WO 2003/034823, U.S. Pat. No. 5,631,072, WO 2005/64072,WO 2006/128870, EP 1724392, WO2005113886 or WO 2007/090739.

Further areas of use of the compositions according to the invention arethe field of tree injection/trunk treatment for all ornamental trees aswell all sort of fruit and nut trees.

In the field of tree injection/trunk treatment, the compounds accordingto the present invention are especially suitable against wood-boringinsects from the order Lepidoptera as mentioned above and from the orderColeoptera, especially against woodborers listed in the following tablesA and B:

TABLE A Examples of exotic woodborers of economic importance. FamilySpecies Host or Crop Infested Buprestidae Agrilus planipennis AshCerambycidae Anoplura glabripennis Hardwoods Scolytidae Xylosandruscrassiusculus Hardwoods X. mutilatus Hardwoods Tomicus piniperdaConifers

TABLE B Examples of native woodborers of economic importance. FamilySpecies Host or Crop Infested Buprestidae Agrilus anxius Birch Agriluspolitus Willow, Maple Agrilus sayi Bayberry, Sweetfern Agrilusvittaticolllis Apple, Pear, Cranberry, Serviceberry, HawthornChrysobothris femorata Apple, Apricot, Beech, Boxelder, Cherry,Chestnut, Currant, Elm, Hawthorn, Hackberry, Hickory, Horsechestnut,Linden, Maple, Mountain-ash, Oak, Pecan, Pear, Peach, Persimmon, Plum,Poplar, Quince, Redbud, Serviceberry, Sycamore, Walnut, Willow Texaniacampestris Basswood, Beech, Maple, Oak, Sycamore, Willow, Yellow-poplarCerambycidae Goes pulverulentus Beech, Elm, Nuttall, Willow, Black oak,Cherrybark oak, Water oak, Sycamore Goes tigrinus Oak Neoclytusacuminatus Ash, Hickory, Oak, Walnut, Birch, Beech, Maple, Easternhophornbeam, Dogwood, Persimmon, Redbud, Holly, Hackberry, Black locust,Honeylocust, Yellow-poplar, Chestnut, Osage-orange, Sassafras, Lilac,Mountain-mahogany, Pear, Cherry, Plum, Peach, Apple, Elm, Basswood,Sweetgum Neoptychodes trilineatus Fig, Alder, Mulberry, Willow, Netleafhackberry Oberea ocellata Sumac, Apple, Peach, Plum, Pear, Currant,Blackberry Oberea tripunctata Dogwood, Viburnum, Elm, Sourwood,Blueberry, Rhododendron, Azalea, Laurel, Poplar, Willow, MulberryOncideres cingulata Hickory, Pecan, Persimmon, Elm, Sourwood, Basswood,Honeylocust, Dogwood, Eucalyptus, Oak, Hackberry, Maple, Fruit treesSaperda calcarata Poplar Strophiona nitens Chestnut, Oak, Hickory,Walnut, Beech, Maple Scolytidae Corthylus columbianus Maple, Oak,Yellow-poplar, Beech, Boxelder, Sycamore, Birch, Basswood, Chestnut, ElmDendroctonus frontalis Pine Dryocoetes betulae Birch, Sweetgum, Wildcherry, Beech, Pear Monarthrum fasciatum Oak, Maple, Birch, Chestnut,Sweetgum, Blackgum, Poplar, Hickory, Mimosa, Apple, Peach, PinePhloeotribus liminaris Peach, Cherry, Plum, Black cherry, Elm, Mulberry,Mountain-ash Pseudopityophthorus pruinosus Oak, American beech, Blackcherry, Chickasaw plum, Chestnut, Maple, Hickory, Hornbeam, HophornbeamSesiidae Paranthrene simulans Oak, American chestnut Sanninauroceriformis Persimmon Synanthedon exitiosa Peach, Plum, Nectarine,Cherry, Apricot, Almond, Black cherry Synanthedon pictipes Peach, Plum,Cherry, Beach, Black Cherry Synanthedon rubrofascia Tupelo Synanthedonscitula Dogwood, Pecan, Hickory, Oak, Chestnut, Beech, Birch, Blackcherry, Elm, Mountain-ash, Viburnum, Willow, Apple, Loquat, Ninebark,Bayberry Vitacea polistiformis Grape

The present invention may be also used to control any insect pests thatmay be present in turfgrass, including for example beetles,caterpillars, fire ants, ground pearls, millipedes, sow bugs, mites,mole crickets, scales, mealybugs ticks, spittlebugs, southern chinchbugs and white grubs. The present invention may be used to controlinsect pests at various stages of their life cycle, including eggs,larvae, nymphs and adults.

In particular, the present invention may be used to control insect peststhat feed on the roots of turfgrass including white grubs (such asCyclocephala spp. (e.g. masked chafer, C. lurida), Rhizotrogus spp.(e.g. European chafer, R. majalis), Cotinus spp. (e.g. Green Junebeetle, C. nitida), Popillia spp. (e.g. Japanese beetle, P. japonica),Phyllophaga spp. (e.g. May/June beetle), Ataenius spp. (e.g. Blackturfgrass ataenius, A. spretulus), Maladera spp. (e.g. Asiatic gardenbeetle, M. castanea) and Tomarus spp.), ground pearls (Margarodes spp.),mole crickets (tawny, southern, and short-winged; Scapteriscus spp.,Gryllotalpa africana) and leatherjackets (European crane fly, Tipulaspp.).

The present invention may also be used to control insect pests ofturfgrass that are thatch dwelling, including armyworms (such as fallarmyworm Spodoptera frugiperda, and common armyworm Pseudaletiaunipuncta), cutworms, billbugs (Sphenophorus spp., such as S. venatusverstitus and S. parvulus), and sod webworms (such as Crambus spp. andthe tropical sod webworm, Herpetogramma phaeopteralis).

The present invention may also be used to control insect pests ofturfgrass that live above the ground and feed on the turfgrass leaves,including chinch bugs (such as southern chinch bugs, Blissus insularis),Bermudagrass mite (Eriophyes cynodoniensis), rhodesgrass mealybug(Antonina graminis), two-lined spittlebug (Propsapia bicincta),leafhoppers, cutworms (Noctuidae family), and greenbugs.

The present invention may also be used to control other pests ofturfgrass such as red imported fire ants (Solenopsis invicta) thatcreate ant mounds in turf.

In the hygiene sector, the compositions according to the invention areactive against ectoparasites such as hard ticks, soft ticks, mangemites, harvest mites, flies (biting and licking), parasitic fly larvae,lice, hair lice, bird lice and fleas.

Examples of such parasites are:

Of the order Anoplurida: Haematopinus spp., Linognathus spp., Pediculusspp. and Phtirus spp., Solenopotes spp.

Of the order Mallophagida: Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

Of the order Diptera and the suborders Nematocerina and Brachycerina,for example Aedes spp., Anopheles spp., Culex spp., Simulium spp.,Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp.,Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopotaspp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossinaspp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp. and Melophagus spp.

Of the order Siphonapterida, for example Pulex spp., Ctenocephalidesspp., Xenopsylla spp., Ceratophyllus spp.

Of the order Heteropterida, for example Cimex spp., Triatoma spp.,Rhodnius spp., Panstrongylus spp.

Of the order Blattarida, for example Blatta orientalis, Periplanetaamericana, Blattelagermanica and Supella spp.

Of the subclass Acaria (Acarida) and the orders Meta- and Meso-stigmata,for example Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp.,Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp.,Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp.,Pneumonyssus spp., Sternostoma spp. and Varroa spp.

Of the orders Actinedida (Prostigmata) and Acaridida (Astigmata), forexample Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobiaspp., Psorergatesspp., Demodex spp., Trombicula spp., Listrophorus spp.,Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp.,Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp.,Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. andLaminosioptes spp.

The compositions according to the invention are also suitable forprotecting against insect infestation in the case of materials such aswood, textiles, plastics, adhesives, glues, paints, paper and card,leather, floor coverings and buildings.

The compositions according to the invention can be used, for example,against the following pests: beetles such as Hylotrupes bajulus,Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum,Ptilinuspecticornis, Dendrobium pertinex, Ernobius mollis, Priobiumcarpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctuslinearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis,Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychuscapucins, Heterobostrychus brunneus, Sinoxylon spec. and Dinoderusminutus, and also hymenopterans such as Sirex juvencus, Urocerus gigas,Urocerus gigas taignus and Urocerus augur, and termites such asKalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermeslucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis andCoptotermes formosanus, and bristletails such as Lepisma saccharina.

The compounds according to the invention can be used as pesticidalagents in unmodified form, but they are generally formulated intocompositions in various ways using formulation adjuvants, such ascarriers, solvents and surface-active substances. The formulations canbe in various physical forms, e.g. in the form of dusting powders, gels,wettable powders, water-dispersible granules, water-dispersible tablets,effervescent pellets, emulsifiable concentrates, microemulsifiableconcentrates, oil-in-water emulsions, oil-flowables, aqueousdispersions, oily dispersions, suspo-emulsions, capsule suspensions,emulsifiable granules, soluble liquids, water-soluble concentrates (withwater or a water-miscible organic solvent as carrier), impregnatedpolymer films or in other forms known e.g. from the Manual onDevelopment and Use of FAO and WHO Specifications for Pesticides, UnitedNations, First Edition, Second Revision (2010). Such formulations caneither be used directly or diluted prior to use. The dilutions can bemade, for example, with water, liquid fertilisers, micronutrients,biological organisms, oil or solvents.

The formulations can be prepared e.g. by mixing the active ingredientwith the formulation adjuvants in order to obtain compositions in theform of finely divided solids, granules, solutions, dispersions oremulsions. The active ingredients can also be formulated with otheradjuvants, such as finely divided solids, mineral oils, oils ofvegetable or animal origin, modified oils of vegetable or animal origin,organic solvents, water, surface-active substances or combinationsthereof.

The active ingredients can also be contained in very fine microcapsules.Microcapsules contain the active ingredients in a porous carrier. Thisenables the active ingredients to be released into the environment incontrolled amounts (e.g. slow-release). Microcapsules usually have adiameter of from 0.1 to 500 microns. They contain active ingredients inan amount of about from 25 to 95% by weight of the capsule weight. Theactive ingredients can be in the form of a monolithic solid, in the formof fine particles in solid or liquid dispersion or in the form of asuitable solution. The encapsulating membranes can comprise, forexample, natural or synthetic rubbers, cellulose, styrene/butadienecopolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides,polyureas, polyurethane or chemically modified polymers and starchxanthates or other polymers that are known to the person skilled in theart. Alternatively, very fine microcapsules can be formed in which theactive ingredient is contained in the form of finely divided particlesin a solid matrix of base substance, but the microcapsules are notthemselves encapsulated.

The formulation adjuvants that are suitable for the preparation of thecompositions according to the invention are known per se. As liquidcarriers there may be used: water, toluene, xylene, petroleum ether,vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acidanhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone,butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkylesters of acetic acid, diacetone alcohol, 1,2-dichloropropane,diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycolabietate, diethylene glycol butyl ether, diethylene glycol ethyl ether,diethylene glycol methyl ether, N,N-dimethylformamide, dimethylsulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methylether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone,ethyl acetate, 2-ethylhexanol, ethylene carbonate,1,1,1-trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyllactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycolmethyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glyceroldiacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamylacetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene,isopropyl myristate, lactic acid, laurylamine, mesityl oxide,methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyllaurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene,n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleicacid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid,propyl lactate, propylene carbonate, propylene glycol, propylene glycolmethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol,xylenesulfonic acid, paraffin, mineral oil, trichloroethylene,perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propyleneglycol methyl ether, diethylene glycol methyl ether, methanol, ethanol,isopropanol, and alcohols of higher molecular weight, such as amylalcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol,propylene glycol, glycerol, N-methyl-2-pyrrolidone and the like.

Suitable solid carriers are, for example, talc, titanium dioxide,pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone,calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks,wheat flour, soybean flour, pumice, wood flour, ground walnut shells,lignin and similar substances.

A large number of surface-active substances can advantageously be usedin both solid and liquid formulations, especially in those formulationswhich can be diluted with a carrier prior to use. Surface-activesubstances may be anionic, cationic, non-ionic or polymeric and they canbe used as emulsifiers, wetting agents or suspending agents or for otherpurposes. Typical surface-active substances include, for example, saltsof alkyl sulfates, such as diethanolammonium lauryl sulfate; salts ofalkylarylsulfonates, such as calcium dodecylbenzenesulfonate;alkylphenol/alkylene oxide addition products, such as nonylphenolethoxylate; alcohol/alkylene oxide addition products, such astridecylalcohol ethoxylate; soaps, such as sodium stearate; salts ofalkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate;dialkyl esters of sulfosuccinate salts, such as sodiumdi(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitololeate; quaternary amines, such as lauryltrimethylammonium chloride,polyethylene glycol esters of fatty acids, such as polyethylene glycolstearate; block copolymers of ethylene oxide and propylene oxide; andsalts of mono- and di-alkylphosphate esters; and also further substancesdescribed e.g. in McCutcheon's Detergents and Emulsifiers Annual, MCPublishing Corp., Ridgewood N.J. (1981).

Further adjuvants that can be used in pesticidal formulations includecrystallisation inhibitors, viscosity modifiers, suspending agents,dyes, anti-oxidants, foaming agents, light absorbers, mixingauxiliaries, antifoams, complexing agents, neutralising or pH-modifyingsubstances and buffers, corrosion inhibitors, fragrances, wettingagents, take-up enhancers, micronutrients, plasticisers, glidants,lubricants, dispersants, thickeners, antifreezes, microbicides, andliquid and solid fertilisers.

The compositions according to the invention can include an additivecomprising an oil of vegetable or animal origin, a mineral oil, alkylesters of such oils or mixtures of such oils and oil derivatives. Theamount of oil additive in the composition according to the invention isgenerally from 0.01 to 10%, based on the mixture to be applied. Forexample, the oil additive can be added to a spray tank in the desiredconcentration after a spray mixture has been prepared. Preferred oiladditives comprise mineral oils or an oil of vegetable origin, forexample rapeseed oil, olive oil or sunflower oil, emulsified vegetableoil, alkyl esters of oils of vegetable origin, for example the methylderivatives, or an oil of animal origin, such as fish oil or beeftallow. Preferred oil additives comprise alkyl esters of C₈-C₂₂ fattyacids, especially the methyl derivatives of C₁₂-C₁₈ fatty acids, forexample the methyl esters of lauric acid, palmitic acid and oleic acid(methyl laurate, methyl palmitate and methyl oleate, respectively). Manyoil derivatives are known from the Compendium of Herbicide Adjuvants,10^(th) Edition, Southern Illinois University, 2010.

The inventive compositions generally comprise from 0.1 to 99% by weight,especially from 0.1 to 95% by weight, of compounds of the presentinvention and from 1 to 99.9% by weight of a formulation adjuvant whichpreferably includes from 0 to 25% by weight of a surface-activesubstance. Whereas commercial products may preferably be formulated asconcentrates, the end user will normally employ dilute formulations.

The rates of application vary within wide limits and depend on thenature of the soil, the method of application, the crop plant, the pestto be controlled, the prevailing climatic conditions, and other factorsgoverned by the method of application, the time of application and thetarget crop. As a general guideline compounds may be applied at a rateof from 1 to 2000 l/ha, especially from 10 to 1000 l/ha.

Preferred formulations can have the following compositions (weight %):

Emulsifiable Concentrates:

active ingredient: 1 to 95%, preferably 60 to 90% surface-active agent:1 to 30%, preferably 5 to 20% liquid carrier: 1 to 80%, preferably 1 to35%

Dusts:

active ingredient: 0.1 to 10%, preferably 0.1 to 5% solid carrier: 99.9to 90%, preferably 99.9 to 99%

Suspension Concentrates:

active ingredient: 5 to 75%, preferably 10 to 50% water: 94 to 24%,preferably 88 to 30% surface-active agent: 1 to 40%, preferably 2 to 30%

Wettable Powders:

active ingredient: 0.5 to 90%, preferably 1 to 80% surface-active agent:0.5 to 20%, preferably 1 to 15% solid carrier: 5 to 95%, preferably 15to 90%

Granules:

active ingredient: 0.1 to 30%, preferably 0.1 to 15% solid carrier: 99.5to 70%, preferably 97 to 85%The following Examples further illustrate, but do not limit, theinvention.

Wettable powders a) b) c) active ingredients 25%  50% 75% sodiumlignosulfonate 5%  5% — sodium lauryl sulfate 3% —  5% sodiumdiisobutylnaphthalenesulfonate —  6% 10% phenol polyethylene glycolether (7-8 mol —  2% — of ethylene oxide) highly dispersed silicic acid5% 10% 10% Kaolin 62%  27% —The combination is thoroughly mixed with the adjuvants and the mixtureis thoroughly ground in a suitable mill, affording wettable powders thatcan be diluted with water to give suspensions of the desiredconcentration.

Powders for dry seed treatment a) b) c) active ingredients 25% 50% 75%light mineral oil  5%  5%  5% highly dispersed silicic acid  5%  5% —Kaolin 65% 40% — Talcum — 20%The combination is thoroughly mixed with the adjuvants and the mixtureis thoroughly ground in a suitable mill, affording powders that can beused directly for seed treatment.

Emulsifiable concentrate active ingredients 10% octylphenol polyethyleneglycol ether (4-5 mol of ethylene 3% oxide) calciumdodecylbenzenesulfonate 3% castor oil polyglycol ether (35 mol ofethylene oxide) 4% Cyclohexanone 30% xylene mixture 50%Emulsions of any required dilution, which can be used in plantprotection, can be obtained from this concentrate by dilution withwater.

Dusts a) b) c) active ingredients  5%  6%  4% Talcum 95% — — Kaolin —94% — mineral filler — — 96%Ready-for-use dusts are obtained by mixing the combination with thecarrier and grinding the mixture in suitable mill. Such powders can alsobe used for dry dressings for seed.

Extruder granules active ingredients 15% sodium lignosulfonate 2%carboxymethylcellulose 1% Kaolin 82%The combination is mixed and ground with the adjuvants, and the mixtureis moistened with water.The mixture is extruded and then dried in a stream of air.

Coated granules active ingredients 8% polyethylene glycol (mol. wt. 200)3% Kaolin 89%The finely ground combination is uniformly applied, in a mixer, to thekaolin moistened with polyethylene glycol. Non-dusty coated granules areobtained in this manner.

Suspension Concentrate

active ingredients 40% propylene glycol 10% nonylphenol polyethyleneglycol ether (15 mol of ethylene oxide) 6% Sodium lignosulfonate 10%carboxymethylcellulose 1% silicone oil (in the form of a 75% emulsion inwater) 1% Water 32%The finely ground combination is intimately mixed with the adjuvants,giving a suspension concentrate from which suspensions of any desireddilution can be obtained by dilution with water. Using such dilutions,living plants as well as plant propagation material can be treated andprotected against infestation by microorganisms, by spraying, pouring orimmersion.

Flowable Concentrate for Seed Treatment

active ingredients 40%  propylene glycol 5% copolymer butanol PO/EO 2%Tristyrenephenole with 10-20 moles EO 2% 1,2-benzisothiazolin-3-one (inthe form of a 20% 0.5%   solution in water) monoazo-pigment calcium salt5% Silicone oil (in the form of a 75% emulsion in water) 0.2%   Water45.3%  The finely ground combination is intimately mixed with the adjuvants,giving a suspension concentrate from which suspensions of any desireddilution can be obtained by dilution with water. Using such dilutions,living plants as well as plant propagation material can be treated andprotected against infestation by microorganisms, by spraying, pouring orimmersion.

Slow Release Capsule Suspension

28 parts of the combination are mixed with 2 parts of an aromaticsolvent and 7 parts of toluenediisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). Thismixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol,0.05 parts of a defoamer and 51.6 parts of water until the desiredparticle size is achieved. To this emulsion a mixture of 2.8 parts1,6-diaminohexane in 5.3 parts of water is added. The mixture isagitated until the polymerization reaction is completed. The obtainedcapsule suspension is stabilized by adding 0.25 parts of a thickener and3 parts of a dispersing agent. The capsule suspension formulationcontains 28% of the active ingredients. The medium capsule diameter is8-15 microns. The resulting formulation is applied to seeds as anaqueous suspension in an apparatus suitable for that purpose.Formulation types include an emulsion concentrate (EC), a suspensionconcentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), awater dispersible granule (WG), an emulsifiable granule (EG), anemulsion, water in oil (EO), an emulsion, oil in water (EW), amicro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable(OF), an oil miscible liquid (OL), a soluble concentrate (SL), anultra-low volume suspension (SU), an ultra-low volume liquid (UL), atechnical concentrate (TK), a dispersible concentrate (DC), a wettablepowder (WP), a soluble granule (SG) or any technically feasibleformulation in combination with agriculturally acceptable adjuvants.The activity of the compositions according to the invention can bebroadened considerably, and adapted to prevailing circumstances, byadding other insecticidally, acaricidally and/or fungicidally activeingredients. The mixtures of the compounds of formula I with otherinsecticidally, acaricidally and/or fungicidally active ingredients mayalso have further surprising advantages which can also be described, ina wider sense, as synergistic activity. For example, better tolerance byplants, reduced phytotoxicity, insects can be controlled in theirdifferent development stages or better behaviour during theirproduction, for example during grinding or mixing, during their storageor during their use. Suitable additions to active ingredients here are,for example, representatives of the following classes of activeingredients: organophosphorus compounds, nitrophenol derivatives,thioureas, juvenile hormones, formamidines, benzophenone derivatives,ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinatedhydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides,neonicotinoids and Bacillus thuringiensis preparations.The following mixtures of the compounds of formula (I) with activeingredients are preferred (the abbreviation “TX” means “one compoundselected from the group consisting of the compounds described in TableA-1 to A-100 and A of the present invention”):an adjuvant selected from the group of substances consisting ofpetroleum oils (alternative name) (628)+TX,an acaricide selected from the group of substances consisting of1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910)+TX,2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts name)(1059)+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name)(1295)+TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981)+TX,abamectin (1)+TX, acequinocyl (3)+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, alpha-cypermethrin(202)+TX, amidithion (870)+TX, amidoflumet [CCN]+TX, amidothioate(872)+TX, amiton (875)+TX, amiton hydrogen oxalate (875)+TX, amitraz(24)+TX, aramite (881)+TX, arsenous oxide (882)+TX, AVI 382 (compoundcode)+TX, AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX,azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX, azocyclotin(46)+TX, azothoate (889)+TX, benomyl (62)+TX, benoxafos (alternativename) [CCN]+TX, benzoximate (71)+TX, benzyl benzoate (IUPAC name)[CCN]+TX, bifenazate (74)+TX, bifenthrin (76)+TX, binapacryl (907)+TX,brofenvalerate (alternative name)+TX, bromocyclen (918)+TX, bromophos(920)+TX, bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin(99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX, butylpyridaben(alternative name)+TX, calcium polysulfide (IUPAC name) (111)+TX,camphechlor (941)+TX, carbanolate (943)+TX, carbaryl (115)+TX,carbofuran (118)+TX, carbophenothion (947)+TX, CGA 50′439 (developmentcode) (125)+TX, chinomethionat (126)+TX, chlorbenside (959)+TX,chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorfenapyr (130)+TX, chlorfenethol (968)+TX, chlorfenson (970)+TX,chlorfensulfide (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate(975)+TX, chloromebuform (977)+TX, chloromethiuron (978)+TX,chloropropylate (983)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl(146)+TX, chlorthiophos (994)+TX, cinerin I (696)+TX, cinerin II(696)+TX, cinerins (696)+TX, clofentezine (158)+TX, closantel(alternative name) [CCN]+TX, coumaphos (174)+TX, crotamiton (alternativename) [CCN]+TX, crotoxyphos (1010)+TX, cufraneb (1013)+TX, cyanthoate(1020)+TX, cyflumetofen (CAS Reg. No.: 400882-07-7)+TX, cyhalothrin(196)+TX, cyhexatin (199)+TX, cypermethrin (201)+TX, DCPM (1032)+TX, DDT(219)+TX, demephion (1037)+TX, demephion-O (1037)+TX, demephion-S(1037)+TX, demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O(1038)+TX, demeton-O-methyl (224)+TX, demeton-S (1038)+TX,demeton-S-methyl (224)+TX, demeton-S-methylsulfon (1039)+TX,diafenthiuron (226)+TX, dialifos (1042)+TX, diazinon (227)+TX,dichlofluanid (230)+TX, dichlorvos (236)+TX, dicliphos (alternativename)+TX, dicofol (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX,dimefox (1081)+TX, dimethoate (262)+TX, dinactin (alternative name)(653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton(269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6 [CCN]+TX,dinocton (1090)+TX, dinopenton (1092)+TX, dinosulfon (1097)+TX,dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl sulfone (IUPACname) (1103)+TX, disulfiram (alternative name) [CCN]+TX, disulfoton(278)+TX, DNOC (282)+TX, dofenapyn (1113)+TX, doramectin (alternativename) [CCN]+TX, endosulfan (294)+TX, endothion (1121)+TX, EPN (297)+TX,eprinomectin (alternative name) [CCN]+TX, ethion (309)+TX,ethoate-methyl (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX,fenazaflor (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX,fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad (alternativename)+TX, fen-pyroximate (345)+TX, fenson (1157)+TX, fentrifanil(1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX, fluacrypyrim(360)+TX, fluazuron (1166)+TX, flubenzimine (1167)+TX, flucycloxuron(366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX, flufenoxuron(370)+TX, flumethrin (372)+TX, fluorbenside (1174)+TX, fluvalinate(1184)+TX, FMC 1137 (development code) (1185)+TX, formetanate (405)+TX,formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate(1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox (424)+TX,heptenophos (432)+TX, hexadecyl cyclopropanecarboxylate (IUPAC/ChemicalAbstracts name) (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPACname) (542)+TX, isocarbophos (alternative name) (473)+TX, isopropylO-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,ivermectin (alternative name) [CCN]+TX, jasmolin 1 (696)+TX, jasmolin 11(696)+TX, jodfenphos (1248)+TX, lindane (430)+TX, lufenuron (490)+TX,malathion (492)+TX, malonoben (1254)+TX, mecarbam (502)+TX, mephosfolan(1261)+TX, mesulfen (alternative name) [CCN]+TX, methacrifos (1266)+TX,methamidophos (527)+TX, methidathion (529)+TX, methiocarb (530)+TX,methomyl (531)+TX, methyl bromide (537)+TX, metolcarb (550)+TX,mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX,milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-512(compound code)+TX, nifluridide (1309)+TX, nikkomycins (alternativename) [CCN]+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloridecomplex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compoundcode)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydeprofos (1324)+TX,oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, parathion (615)+TX,permethrin (626)+TX, petroleum oils (alternative name) (628)+TX,phenkapton (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone(637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon (639)+TX,phoxim (642)+TX, pirimiphos-methyl (652)+TX, polychloroterpenes(traditional name) (1347)+TX, polynactins (alternative name) (653)+TX,proclonol (1350)+TX, profenofos (662)+TX, promacyl (1354)+TX, propargite(671)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion(1360)+TX, prothoate (1362)+TX, pyrethrin 1 (696)+TX, pyrethrin II(696)+TX, pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion(701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos(711)+TX, quintiofos (1381)+TX, R-1492 (development code) (1382)+TX,RA-17 (development code) (1383)+TX, rotenone (722)+TX, schradan(1389)+TX, sebufos (alternative name)+TX, selamectin (alternative name)[CCN]+TX, SI-0009 (compound code)+TX, sophamide (1402)+TX, spirodiclofen(738)+TX, spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX,sulfiram (alternative name) [CCN]+TX, sulfluramid (750)+TX, sulfotep(753)+TX, sulfur (754)+TX, SZI-121 (development code) (757)+TX,tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP (1417)+TX, terbam(alternative name)+TX, tetrachlorvinphos (777)+TX, tetradifon (786)+TX,tetranactin (alternative name) (653)+TX, tetrasul (1425)+TX, thiafenox(alternative name)+TX, thiocarboxime (1431)+TX, thiofanox (800)+TX,thiometon (801)+TX, thioquinox (1436)+TX, thuringiensin (alternativename) [CCN]+TX, triamiphos (1441)+TX, triarathene (1443)+TX, triazophos(820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX,trifenofos (1455)+TX, trinactin (alternative name) (653)+TX, vamidothion(847)+TX, vaniliprole [CCN] and YI-5302 (compound code)+TX, an algicideselected from the group of substances consisting of bethoxazin [CCN]+TX,copper dioctanoate (IUPAC name) (170)+TX, copper sulfate (172)+TX,cybutryne [CCN]+TX, dichlone (1052)+TX, dichlorophen (232)+TX, endothal(295)+TX, fentin (347)+TX, hydrated lime [CCN]+TX, nabam (566)+TX,quinoclamine (714)+TX, quinonamid (1379)+TX, simazine (730)+TX,triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide(IUPAC name) (347)+TX, an anthelmintic selected from the group ofsubstances consisting of abamectin (1)+TX, crufomate (1011)+TX,doramectin (alternative name) [CCN]+TX, emamectin (291)+TX, emamectinbenzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX, ivermectin(alternative name) [CCN]+TX, milbemycin oxime (alternative name)[CCN]+TX, moxidectin (alternative name) [CCN]+TX, piperazine [CCN]+TX,selamectin (alternative name) [CCN]+TX, spinosad (737) and thiophanate(1435)+TX,an avicide selected from the group of substances consisting ofchloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX,pyridin-4-amine (IUPAC name) (23) and strychnine (745)+TX,a bactericide selected from the group of substances consisting of1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX, copperdioctanoate (IUPAC name) (170)+TX, copper hydroxide (IUPAC name)(169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX, dipyrithione(1105)+TX, dodicin (1112)+TX, fenaminosulf (1144)+TX, formaldehyde(404)+TX, hydrargaphen (alternative name) [CCN]+TX, kasugamycin(483)+TX, kasugamycin hydrochloride hydrate (483)+TX, nickelbis(dimethyldithiocarbamate) (IUPAC name) (1308)+TX, nitrapyrin(580)+TX, octhilinone (590)+TX, oxolinic acid (606)+TX, oxytetracycline(611)+TX, potassium hydroxyquinoline sulfate (446)+TX, probenazole(658)+TX, streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX,tecloftalam (766)+TX, and thiomersal (alternative name) [CCN]+TX,a biological agent selected from the group of substances consisting ofAdoxophyes orana GV (alternative name) (12)+TX, Agrobacteriumradiobacter (alternative name) (13)+TX, Amblyseius spp. (alternativename) (19)+TX, Anagrapha falcifera NPV (alternative name) (28)+TX,Anagrus atomus (alternative name) (29)+TX, Aphelinus abdominalis(alternative name) (33)+TX, Aphidius colemani (alternative name)(34)+TX, Aphidoletes aphidimyza (alternative name) (35)+TX, Autographacalifornica NPV (alternative name) (38)+TX, Bacillus firmus (alternativename) (48)+TX, Bacillus sphaericus Neide (scientific name) (49)+TX,Bacillus thuringiensis Berliner (scientific name) (51)+TX, Bacillusthuringiensis subsp. aizawai (scientific name) (51)+TX, Bacillusthuringiensis subsp. israelensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. japonensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. kurstaki (scientific name) (51)+TX, Bacillusthuringiensis subsp. tenebrionis (scientific name) (51)+TX, Beauveriabassiana (alternative name) (53)+TX, Beauveria brongniartii (alternativename) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX,Cryptolaemus montrouzieri (alternative name) (178)+TX, Cydia pomonellaGV (alternative name) (191)+TX, Dacnusa sibirica (alternative name)(212)+TX, Diglyphus isaea (alternative name) (254)+TX, Encarsia formosa(scientific name) (293)+TX, Eretmocerus eremicus (alternative name)(300)+TX, Helicoverpa zea NPV (alternative name) (431)+TX,Heterorhabditis bacteriophora and H. megidis (alternative name)(433)+TX, Hippodamia convergens (alternative name) (442)+TX, Leptomastixdactylopii (alternative name) (488)+TX, Macrolophus caliginosus(alternative name) (491)+TX, Mamestra brassicae NPV (alternative name)(494)+TX, Metaphycus helvolus (alternative name) (522)+TX, Metarhiziumanisopliae var. acridum (scientific name) (523)+TX, Metarhiziumanisopliae var. anisopliae (scientific name) (523)+TX, Neodiprionsertifer NPV and N. lecontei NPV (alternative name) (575)+TX, Orius spp.(alternative name) (596)+TX, Paecilomyces fumosoroseus (alternativename) (613)+TX, Phytoseiulus persimilis (alternative name) (644)+TX,Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientificname) (741)+TX, Steinernema bibionis (alternative name) (742)+TX,Steinernema carpocapsae (alternative name) (742)+TX, Steinernema feltiae(alternative name) (742)+TX, Steinernema glaseri (alternative name)(742)+TX, Steinernema riobrave (alternative name) (742)+TX, Steinernemariobravis (alternative name) (742)+TX, Steinernema scapterisci(alternative name) (742)+TX, Steinernema spp. (alternative name)(742)+TX, Trichogramma spp. (alternative name) (826)+TX, Typhlodromusoccidentalis (alternative name) (844) and Verticillium lecanii(alternative name) (848)+TX,a soil sterilant selected from the group of substances consisting ofiodomethane (IUPAC name) (542) and methyl bromide (537)+TX,a chemosterilant selected from the group of substances consisting ofapholate [CCN]+TX, bisazir (alternative name) [CCN]+TX, busulfan(alternative name) [CCN]+TX, diflubenzuron (250)+TX, dimatif(alternative name) [CCN]+TX, hemel [CCN]+TX, hempa [CCN]+TX, metepa[CCN]+TX, methiotepa [CCN]+TX, methyl apholate [CCN]+TX, morzid[CCN]+TX, penfluron (alternative name) [CCN]+TX, tepa [CCN]+TX,thiohempa (alternative name) [CCN]+TX, thiotepa (alternative name)[CCN]+TX, tretamine (alternative name) [CCN] and uredepa (alternativename) [CCN]+TX,an insect pheromone selected from the group of substances consisting of(E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (IUPAC name) (222)+TX,(E)-tridec-4-en-1-yl acetate (IUPAC name) (829)+TX,(E)-6-methylhept-2-en-4-ol (IUPAC name) (541)+TX,(E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779)+TX,(Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX, (Z)-hexadec-11-enal(IUPAC name) (436)+TX, (Z)-hexadec-11-en-1-yl acetate (IUPAC name)(437)+TX, (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX,(Z)-icos-13-en-10-one (IUPAC name) (448)+TX, (Z)-tetradec-7-en-1-al(IUPAC name) (782)+TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX,(Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784)+TX,(7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283)+TX,(9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780)+TX,(9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781)+TX,14-methyloctadec-1-ene (IUPAC name) (545)+TX, 4-methylnonan-5-ol with4-methylnonan-5-one (IUPAC name) (544)+TX, alpha-multistriatin(alternative name) [CCN]+TX, brevicomin (alternative name) [CCN]+TX,codlelure (alternative name) [CCN]+TX, codlemone (alternative name)(167)+TX, cuelure (alternative name) (179)+TX, disparlure (277)+TX,dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl acetate(IUPAC name) (287)+TX, dodeca-8+TX, 10-dien-1-yl acetate (IUPAC name)(284)+TX, dominicalure (alternative name) [CCN]+TX, ethyl4-methyloctanoate (IUPAC name) (317)+TX, eugenol (alternative name)[CCN]+TX, frontalin (alternative name) [CCN]+TX, gossyplure (alternativename) (420)+TX, grandlure (421)+TX, grandlure I (alternative name)(421)+TX, grandlure II (alternative name) (421)+TX, grandlure III(alternative name) (421)+TX, grandlure IV (alternative name) (421)+TX,hexalure [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol(alternative name) [CCN]+TX, japonilure (alternative name) (481)+TX,lineatin (alternative name) [CCN]+TX, litlure (alternative name)[CCN]+TX, looplure (alternative name) [CCN]+TX, medlure [CCN]+TX,megatomoic acid (alternative name) [CCN]+TX, methyl eugenol (alternativename) (540)+TX, muscalure (563)+TX, octadeca-2,13-dien-1-yl acetate(IUPAC name) (588)+TX, octadeca-3,13-dien-1-yl acetate (IUPAC name)(589)+TX, orfralure (alternative name) [CCN]+TX, oryctalure (alternativename) (317)+TX, ostramone (alternative name) [CCN]+TX, siglure [CCN]+TX,sordidin (alternative name) (736)+TX, sulcatol (alternative name)[CCN]+TX, tetradec-11-en-1-yl acetate (IUPAC name) (785)+TX, trimedlure(839)+TX, trimedlure A (alternative name) (839)+TX, trimedlure Bi(alternative name) (839)+TX, trimedlure B₂ (alternative name) (839)+TX,trimedlure C (alternative name) (839) and trunc-call (alternative name)[CCN]+TX,an insect repellent selected from the group of substances consisting of2-(octylthio)ethanol (IUPAC name) (591)+TX, butopyronoxyl (933)+TX,butoxy(polypropylene glycol) (936)+TX, dibutyl adipate (IUPAC name)(1046)+TX, dibutyl phthalate (1047)+TX, dibutyl succinate (IUPAC name)(1048)+TX, diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX,dimethyl phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide[CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide [CCN]+TX,oxamate [CCN] and picaridin [CCN]+TX, an insecticide selected from thegroup of substances consisting of 1-dichloro-1-nitroethane(IUPAC/Chemical Abstracts name) (1058)+TX,1,1-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056), +TX,1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX,1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063)+TX,1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916)+TX,2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name)(1451)+TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate(IUPAC name) (1066)+TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate(IUPAC/Chemical Abstracts name) (1109)+TX, 2-(2-butoxyethoxy)ethylthiocyanate (IUPAC/Chemical Abstracts name) (935)+TX,2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (IUPAC/ChemicalAbstracts name) (1084)+TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name)(986)+TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX,2-imidazolidone (IUPAC name) (1225)+TX, 2-isovalerylindan-1,3-dione(IUPAC name) (1246)+TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate(IUPAC name) (1284)+TX, 2-thiocyanatoethyl laurate (IUPAC name)(1433)+TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917)+TX,3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283)+TX,4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name)(1285)+TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPACname) (1085)+TX, abamectin (1)+TX, acephate (2)+TX, acetamiprid (4)+TX,acethion (alternative name) [CCN]+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, acrylonitrile (IUPAC name) (861)+TX, alanycarb (15)+TX, aldicarb(16)+TX, aldoxycarb (863)+TX, aldrin (864)+TX, allethrin (17)+TX,allosamidin (alternative name) [CCN]+TX, allyxycarb (866)+TX,alpha-cypermethrin (202)+TX, alpha-ecdysone (alternative name) [CCN]+TX,aluminium phosphide (640)+TX, amidithion (870)+TX, amidothioate(872)+TX, aminocarb (873)+TX, amiton (875)+TX, amiton hydrogen oxalate(875)+TX, amitraz (24)+TX, anabasine (877)+TX, athidathion (883)+TX, AVI382 (compound code)+TX, AZ 60541 (compound code)+TX, azadirachtin(alternative name) (41)+TX, azamethiphos (42)+TX, azinphos-ethyl(44)+TX, azinphos-methyl (45)+TX, azothoate (889)+TX, Bacillusthuringiensis delta endotoxins (alternative name) (52)+TX, bariumhexafluorosilicate (alternative name) [CCN]+TX, barium polysulfide(IUPAC/Chemical Abstracts name) (892)+TX, barthrin [CCN]+TX, Bayer22/190 (development code) (893)+TX, Bayer 22408 (development code)(894)+TX, bendiocarb (58)+TX, benfuracarb (60)+TX, bensultap (66)+TX,beta-cyfluthrin (194)+TX, beta-cypermethrin (203)+TX, bifenthrin(76)+TX, bioallethrin (78)+TX, bioallethrin S-cyclopentenyl isomer(alternative name) (79)+TX, bioethanomethrin [CCN]+TX, biopermethrin(908)+TX, bioresmethrin (80)+TX, bis(2-chloroethyl) ether (IUPAC name)(909)+TX, bistrifluron (83)+TX, borax (86)+TX, brofenvalerate(alternative name)+TX, bromfenvinfos (914)+TX, bromocyclen (918)+TX,bromo-DDT (alternative name) [CCN]+TX, bromophos (920)+TX,bromophos-ethyl (921)+TX, bufencarb (924)+TX, buprofezin (99)+TX,butacarb (926)+TX, butathiofos (927)+TX, butocarboxim (103)+TX, butonate(932)+TX, butoxycarboxim (104)+TX, butylpyridaben (alternative name)+TX,cadusafos (109)+TX, calcium arsenate [CCN]+TX, calcium cyanide (444)+TX,calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX,carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX, carbondisulfide (IUPAC/Chemical Abstracts name) (945)+TX, carbon tetrachloride(IUPAC name) (946)+TX, carbophenothion (947)+TX, carbosulfan (119)+TX,cartap (123)+TX, cartap hydrochloride (123)+TX, cevadine (alternativename) (725)+TX, chlorbicyclen (960)+TX, chlordane (128)+TX, chlordecone(963)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorethoxyfos (129)+TX, chlorfenapyr (130)+TX, chlorfenvinphos(131)+TX, chlorfluazuron (132)+TX, chlormephos (136)+TX, CDCl3 [CCN]+TX,chloropicrin (141)+TX, chlorphoxim (989)+TX, chlorprazophos (990)+TX,chlorpyrifos (145)+TX, chlorpyrifos-methyl (146)+TX, chlorthiophos(994)+TX, chromafenozide (150)+TX, cinerin I (696)+TX, cinerin II(696)+TX, cinerins (696)+TX, cis-resmethrin (alternative name)+TX,cismethrin (80)+TX, clocythrin (alternative name)+TX, cloethocarb(999)+TX, closantel (alternative name) [CCN]+TX, clothianidin (165)+TX,copper acetoarsenite [CCN]+TX, copper arsenate [CCN]+TX, copper oleate[CCN]+TX, coumaphos (174)+TX, coumithoate (1006)+TX, crotamiton(alternative name) [CCN]+TX, crotoxyphos (1010)+TX, crufomate (1011)+TX,cryolite (alternative name) (177)+TX, CS 708 (development code)(1012)+TX, cyanofenphos (1019)+TX, cyanophos (184)+TX, cyanthoate(1020)+TX, cyclethrin [CCN]+TX, cycloprothrin (188)+TX, cyfluthrin(193)+TX, cyhalothrin (196)+TX, cypermethrin (201)+TX, cyphenothrin(206)+TX, cyromazine (209)+TX, cythioate (alternative name) [CCN]+TX,d-limonene (alternative name) [CCN]+TX, d-tetramethrin (alternativename) (788)+TX, DAEP (1031)+TX, dazomet (216)+TX, DDT (219)+TX,decarbofuran (1034)+TX, deltamethrin (223)+TX, demephion (1037)+TX,demephion-O (1037)+TX, demephion-S (1037)+TX, demeton (1038)+TX,demeton-methyl (224)+TX, demeton-O (1038)+TX, demeton-O-methyl (224)+TX,demeton-S (1038)+TX, demeton-S-methyl (224)+TX, demeton-S-methylsulphon(1039)+TX, diafenthiuron (226)+TX, dialifos (1042)+TX, diamidafos(1044)+TX, diazinon (227)+TX, dicapthon (1050)+TX, dichlofenthion(1051)+TX, dichlorvos (236)+TX, dicliphos (alternative name)+TX,dicresyl (alternative name) [CCN]+TX, dicrotophos (243)+TX, dicyclanil(244)+TX, dieldrin (1070)+TX, diethyl 5-methylpyrazol-3-yl phosphate(IUPAC name) (1076)+TX, diflubenzuron (250)+TX, dilor (alternative name)[CCN]+TX, dimefluthrin [CCN]+TX, dimefox (1081)+TX, dimetan (1085)+TX,dimethoate (262)+TX, dimethrin (1083)+TX, dimethylvinphos (265)+TX,dimetilan (1086)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX,dinoprop (1093)+TX, dinosam (1094)+TX, dinoseb (1095)+TX, dinotefuran(271)+TX, diofenolan (1099)+TX, dioxabenzofos (1100)+TX, dioxacarb(1101)+TX, dioxathion (1102)+TX, disulfoton (278)+TX, dithicrofos(1108)+TX, DNOC (282)+TX, doramectin (alternative name) [CCN]+TX, DSP(1115)+TX, ecdysterone (alternative name) [CCN]+TX, EI 1642 (developmentcode) (1118)+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, EMPC(1120)+TX, empenthrin (292)+TX, endosulfan (294)+TX, endothion(1121)+TX, endrin (1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane(1124)+TX, eprinomectin (alternative name) [CCN]+TX, esfenvalerate(302)+TX, etaphos (alternative name) [CCN]+TX, ethiofencarb (308)+TX,ethion (309)+TX, ethiprole (310)+TX, ethoate-methyl (1134)+TX,ethoprophos (312)+TX, ethyl formate (IUPAC name) [CCN]+TX, ethyl-DDD(alternative name) (1056)+TX, ethylene dibromide (316)+TX, ethylenedichloride (chemical name) (1136)+TX, ethylene oxide [CCN]+TX,etofenprox (319)+TX, etrimfos (1142)+TX, EXD (1143)+TX, famphur(323)+TX, fenamiphos (326)+TX, fenazaflor (1147)+TX, fenchlorphos(1148)+TX, fenethacarb (1149)+TX, fenfluthrin (1150)+TX, fenitrothion(335)+TX, fenobucarb (336)+TX, fenoxacrim (1153)+TX, fenoxycarb(340)+TX, fenpirithrin (1155)+TX, fenpropathrin (342)+TX, fenpyrad(alternative name)+TX, fensulfothion (1158)+TX, fenthion (346)+TX,fenthion-ethyl [CCN]+TX, fenvalerate (349)+TX, fipronil (354)+TX,flonicamid (358)+TX, flubendiamide (CAS. Reg. No.: 272451-65-7)+TX,flucofuron (1168)+TX, flucycloxuron (366)+TX, flucythrinate (367)+TX,fluenetil (1169)+TX, flufenerim [CCN]+TX, flufenoxuron (370)+TX,flufenprox (1171)+TX, flumethrin (372)+TX, fluvalinate (1184)+TX, FMC1137 (development code) (1185)+TX, fonofos (1191)+TX, formetanate(405)+TX, formetanate hydrochloride (405)+TX, formothion (1192)+TX,formparanate (1193)+TX, fosmethilan (1194)+TX, fospirate (1195)+TX,fosthiazate (408)+TX, fosthietan (1196)+TX, furathiocarb (412)+TX,furethrin (1200)+TX, gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX,guazatine (422)+TX, guazatine acetates (422)+TX, GY-81 (developmentcode) (423)+TX, halfenprox (424)+TX, halofenozide (425)+TX, HCH(430)+TX, HEOD (1070)+TX, heptachlor (1211)+TX, heptenophos (432)+TX,heterophos [CCN]+TX, hexaflumuron (439)+TX, HHDN (864)+TX,hydramethylnon (443)+TX, hydrogen cyanide (444)+TX, hydroprene (445)+TX,hyquincarb (1223)+TX, imidacloprid (458)+TX, imiprothrin (460)+TX,indoxacarb (465)+TX, iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX,isazofos (1231)+TX, isobenzan (1232)+TX, isocarbophos (alternative name)(473)+TX, isodrin (1235)+TX, isofenphos (1236)+TX, isolane (1237)+TX,isoprocarb (472)+TX, isopropyl O-(methoxy-aminothiophosphoryl)salicylate(IUPAC name) (473)+TX, isoprothiolane (474)+TX, isothioate (1244)+TX,isoxathion (480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin 1(696)+TX, jasmolin 11 (696)+TX, jodfenphos (1248)+TX, juvenile hormone I(alternative name) [CCN]+TX, juvenile hormone II (alternative name)[CCN]+TX, juvenile hormone Ill (alternative name) [CCN]+TX, kelevan(1249)+TX, kinoprene (484)+TX, lambda-cyhalothrin (198)+TX, leadarsenate [CCN]+TX, lepimectin (CCN)+TX, leptophos (1250)+TX, lindane(430)+TX, lirimfos (1251)+TX, lufenuron (490)+TX, lythidathion(1253)+TX, m-cumenyl methylcarbamate (IUPAC name) (1014)+TX, magnesiumphosphide (IUPAC name) (640)+TX, malathion (492)+TX, malonoben(1254)+TX, mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX,menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride (513)+TX,mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam (519)+TX,metam-potassium (alternative name) (519)+TX, metam-sodium (519)+TX,methacrifos (1266)+TX, methamidophos (527)+TX, methanesulfonyl fluoride(IUPAC/Chemical Abstracts name) (1268)+TX, methidathion (529)+TX,methiocarb (530)+TX, methocrotophos (1273)+TX, methomyl (531)+TX,methoprene (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternativename) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX, methylbromide (537)+TX, methyl isothiocyanate (543)+TX, methylchloroform(alternative name) [CCN]+TX, methylene chloride [CCN]+TX, metofluthrin[CCN]+TX, metolcarb (550)+TX, metoxadiazone (1288)+TX, mevinphos(556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime(alternative name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naftalofos (alternative name) [CCN]+TX, naled (567)+TX,naphthalene (IUPAC/Chemical Abstracts name) (1303)+TX, NC-170(development code) (1306)+TX, NC-184 (compound code)+TX, nicotine(578)+TX, nicotine sulfate (578)+TX, nifluridide (1309)+TX, nitenpyram(579)+TX, nithiazine (1311)+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250(compound code)+TX, nornicotine (traditional name) (1319)+TX, novaluron(585)+TX, noviflumuron (586)+TX, O-5-dichloro-4-iodophenyl O-ethylethylphosphonothioate (IUPAC name) (1057)+TX, O,O-diethylO-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate (IUPAC name)(1074)+TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-ylphosphorothioate (IUPAC name) (1075)+TX, O,O,O′,O′-tetrapropyldithiopyrophosphate (IUPAC name) (1424)+TX, oleic acid (IUPAC name)(593)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydemeton-methyl(609)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT(219)+TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX,parathion-methyl (616)+TX, penfluron (alternative name) [CCN]+TX,pentachlorophenol (623)+TX, pentachlorophenyl laurate (IUPAC name)(623)+TX, permethrin (626)+TX, petroleum oils (alternative name)(628)+TX, PH 60-38 (development code) (1328)+TX, phenkapton (1330)+TX,phenothrin (630)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone(637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX,phosphamidon (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX,phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, pirimicarb (651)+TX,pirimiphos-ethyl (1345)+TX, pirimiphos-methyl (652)+TX,polychlorodicyclopentadiene isomers (IUPAC name) (1346)+TX,polychloroterpenes (traditional name) (1347)+TX, potassium arsenite[CCN]+TX, potassium thiocyanate [CCN]+TX, prallethrin (655)+TX,precocene I (alternative name) [CCN]+TX, precocene II (alternative name)[CCN]+TX, precocene III (alternative name) [CCN]+TX, primidophos(1349)+TX, profenofos (662)+TX, profluthrin [CCN]+TX, promacyl(1354)+TX, promecarb (1355)+TX, propaphos (1356)+TX, propetamphos(673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothiofos(686)+TX, prothoate (1362)+TX, protrifenbute [CCN]+TX, pymetrozine(688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX, pyresmethrin(1367)+TX, pyrethrin 1 (696)+TX, pyrethrin II (696)+TX, pyrethrins(696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX, pyridaphenthion(701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, pyriproxyfen(708)+TX, quassia (alternative name) [CCN]+TX, quinalphos (711)+TX,quinalphos-methyl (1376)+TX, quinothion (1380)+TX, quintiofos (1381)+TX,R-1492 (development code) (1382)+TX, rafoxanide (alternative name)[CCN]+TX, resmethrin (719)+TX, rotenone (722)+TX, RU 15525 (developmentcode) (723)+TX, RU 25475 (development code) (1386)+TX, ryania(alternative name) (1387)+TX, ryanodine (traditional name) (1387)+TX,sabadilla (alternative name) (725)+TX, schradan (1389)+TX, sebufos(alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009(compound code)+TX, SI-0205 (compound code)+TX, SI-0404 (compoundcode)+TX, SI-0405 (compound code)+TX, silafluofen (728)+TX, SN 72129(development code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide(444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name) (1399)+TX,sodium hexafluorosilicate (1400)+TX, sodium pentachlorophenoxide(623)+TX, sodium selenate (IUPAC name) (1401)+TX, sodium thiocyanate[CCN]+TX, sophamide (1402)+TX, spinosad (737)+TX, spiromesifen (739)+TX,spirotetrmat (CCN)+TX, sulcofuron (746)+TX, sulcofuron-sodium (746)+TX,sulfluramid (750)+TX, sulfotep (753)+TX, sulfuryl fluoride (756)+TX,sulprofos (1408)+TX, tar oils (alternative name) (758)+TX,tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE (1414)+TX,tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos (764)+TX,teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos (770)+TX, TEPP(1417)+TX, terallethrin (1418)+TX, terbam (alternative name)+TX,terbufos (773)+TX, tetrachloroethane [CCN]+TX, tetrachlorvinphos(777)+TX, tetramethrin (787)+TX, theta-cypermethrin (204)+TX,thiacloprid (791)+TX, thiafenox (alternative name)+TX, thiamethoxam(792)+TX, thicrofos (1428)+TX, thiocarboxime (1431)+TX, thiocyclam(798)+TX, thiocyclam hydrogen oxalate (798)+TX, thiodicarb (799)+TX,thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX, thiosultap(803)+TX, thiosultap-sodium (803)+TX, thuringiensin (alternative name)[CCN]+TX, tolfenpyrad (809)+TX, tralomethrin (812)+TX, transfluthrin(813)+TX, transpermethrin (1440)+TX, triamiphos (1441)+TX, triazamate(818)+TX, triazophos (820)+TX, triazuron (alternative name)+TX,trichlorfon (824)+TX, trichlormetaphos-3 (alternative name) [CCN]+TX,trichloronat (1452)+TX, trifenofos (1455)+TX, triflumuron (835)+TX,trimethacarb (840)+TX, triprene (1459)+TX, vamidothion (847)+TX,vaniliprole [CCN]+TX, veratridine (alternative name) (725)+TX, veratrine(alternative name) (725)+TX, XMC (853)+TX, xylylcarb (854)+TX, YI-5302(compound code)+TX, zeta-cypermethrin (205)+TX, zetamethrin (alternativename)+TX, zinc phosphide (640)+TX, zolaprofos (1469) and ZXI 8901(development code) (858)+TX, cyantraniliprole [736994-63-19+TX,chlorantraniliprole [500008-45-7]+TX, cyenopyrafen [560121-52-0]+TX,cyflumetofen [400882-07-7]+TX, pyrifluquinazon [337458-27-2]+TX,spinetoram [187166-40-1+187166-15-0]+TX, spirotetramat [203313-25-1]+TX,sulfoxaflor [946578-00-3]+TX, flufiprole [704886-18-0]+TX, meperfluthrin[915288-13-0]+TX, tetramethylfluthrin [84937-88-2]+TX, triflumezopyrim(disclosed in WO 2012/092115)+TX, fluxametamide (WO 2007/026965)+TX,epsilon-metofluthrin [240494-71-7]+TX, epsilon-momfluorothrin[1065124-65-3]+TX, fluazaindolizine [1254304-22-7]+TX, chloroprallethrin[399572-87-3]+TX, fluxametamide [928783-29-3]+TX, cyhalodiamide[1262605-53-7]+TX, tioxazafen [330459-31-9]+TX, broflanilide[1207727-04-5]+TX, flufiprole [704886-18-0]+TX, cyclaniliprole[1031756-98-5]+TX, tetraniliprole [1229654-66-3]+TX, guadipyr (describedin WO2010/060231)+TX, cycloxaprid (described in WO2005/077934)+TX,a molluscicide selected from the group of substances consisting ofbis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide [CCN]+TX,calcium arsenate [CCN]+TX, cloethocarb (999)+TX, copper acetoarsenite[CCN]+TX, copper sulfate (172)+TX, fentin (347)+TX, ferric phosphate(IUPAC name) (352)+TX, metaldehyde (518)+TX, methiocarb (530)+TX,niclosamide (576)+TX, niclosamide-olamine (576)+TX, pentachlorophenol(623)+TX, sodium pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX,thiodicarb (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX,trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347) andtriphenyltin hydroxide (IUPAC name) (347)+TX, pyriprole[394730-71-3]+TX,a nematicide selected from the group of substances consisting ofAKD-3088 (compound code)+TX, 1,2-dibromo-3-chloropropane (IUPAC/ChemicalAbstracts name) (1045)+TX, 1,2-dichloropropane (IUPAC/Chemical Abstractsname) (1062)+TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPACname) (1063)+TX, 1,3-dichloropropene (233)+TX,3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC/Chemical Abstractsname) (1065)+TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name)(980)+TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPACname) (1286)+TX, 6-isopentenylaminopurine (alternative name) (210)+TX,abamectin (1)+TX, acetoprole [CCN]+TX, alanycarb (15)+TX, aldicarb(16)+TX, aldoxycarb (863)+TX, AZ 60541 (compound code)+TX, benclothiaz[CCN]+TX, benomyl (62)+TX, butylpyridaben (alternative name)+TX,cadusafos (109)+TX, carbofuran (118)+TX, carbon disulfide (945)+TX,carbosulfan (119)+TX, chloropicrin (141)+TX, chlorpyrifos (145)+TX,cloethocarb (999)+TX, cytokinins (alternative name) (210)+TX, dazomet(216)+TX, DBCP (1045)+TX, DCIP (218)+TX, diamidafos (1044)+TX,dichlofenthion (1051)+TX, dicliphos (alternative name)+TX, dimethoate(262)+TX, doramectin (alternative name) [CCN]+TX, emamectin (291)+TX,emamectin benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX,ethoprophos (312)+TX, ethylene dibromide (316)+TX, fenamiphos (326)+TX,fenpyrad (alternative name)+TX, fensulfothion (1158)+TX, fosthiazate(408)+TX, fosthietan (1196)+TX, furfural (alternative name) [CCN]+TX,GY-81 (development code) (423)+TX, heterophos [CCN]+TX, iodomethane(IUPAC name) (542)+TX, isamidofos (1230)+TX, isazofos (1231)+TX,ivermectin (alternative name) [CCN]+TX, kinetin (alternative name)(210)+TX, mecarphon (1258)+TX, metam (519)+TX, metam-potassium(alternative name) (519)+TX, metam-sodium (519)+TX, methyl bromide(537)+TX, methyl isothiocyanate (543)+TX, milbemycin oxime (alternativename) [CCN]+TX, moxidectin (alternative name) [CCN]+TX, Myrotheciumverrucaria composition (alternative name) (565)+TX, NC-184 (compoundcode)+TX, oxamyl (602)+TX, phorate (636)+TX, phosphamidon (639)+TX,phosphocarb [CCN]+TX, sebufos (alternative name)+TX, selamectin(alternative name) [CCN]+TX, spinosad (737)+TX, terbam (alternativename)+TX, terbufos (773)+TX, tetrachlorothiophene (IUPAC/ChemicalAbstracts name) (1422)+TX, thiafenox (alternative name)+TX, thionazin(1434)+TX, triazophos (820)+TX, triazuron (alternative name)+TX,xylenols [CCN]+TX, YI-5302 (compound code) and zeatin (alternative name)(210)+TX, fluensulfone [318290-98-1]+TX,a nitrification inhibitor selected from the group of substancesconsisting of potassium ethylxanthate [CCN] and nitrapyrin (580)+TX,a plant activator selected from the group of substances consisting ofacibenzolar (6)+TX, acibenzolar-S-methyl (6)+TX, probenazole (658) andReynoutria sachalinensis extract (alternative name) (720)+TX,a rodenticide selected from the group of substances consisting of2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,alpha-chlorohydrin [CCN]+TX, aluminium phosphide (640)+TX, antu(880)+TX, arsenous oxide (882)+TX, barium carbonate (891)+TX,bisthiosemi (912)+TX, brodifacoum (89)+TX, bromadiolone (91)+TX,bromethalin (92)+TX, calcium cyanide (444)+TX, chloralose (127)+TX,chlorophacinone (140)+TX, cholecalciferol (alternative name) (850)+TX,coumachlor (1004)+TX, coumafuryl (1005)+TX, coumatetralyl (175)+TX,crimidine (1009)+TX, difenacoum (246)+TX, difethialone (249)+TX,diphacinone (273)+TX, ergocalciferol (301)+TX, flocoumafen (357)+TX,fluoroacetamide (379)+TX, flupropadine (1183)+TX, flupropadinehydrochloride (1183)+TX, gamma-HCH (430)+TX, HCH (430)+TX, hydrogencyanide (444)+TX, iodomethane (IUPAC name) (542)+TX, lindane (430)+TX,magnesium phosphide (IUPAC name) (640)+TX, methyl bromide (537)+TX,norbormide (1318)+TX, phosacetim (1336)+TX, phosphine (IUPAC name)(640)+TX, phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite[CCN]+TX, pyrinuron (1371)+TX, scilliroside (1390)+TX, sodium arsenite[CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate (735)+TX,strychnine (745)+TX, thallium sulfate [CCN]+TX, warfarin (851) and zincphosphide (640)+TX,a synergist selected from the group of substances consisting of2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934)+TX,5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903)+TX,farnesol with nerolidol (alternative name) (324)+TX, MB-599 (developmentcode) (498)+TX, MGK 264 (development code) (296)+TX, piperonyl butoxide(649)+TX, piprotal (1343)+TX, propyl isomer (1358)+TX, S421 (developmentcode) (724)+TX, sesamex (1393)+TX, sesasmolin (1394) and sulfoxide(1406)+TX,an animal repellent selected from the group of substances consisting ofanthraquinone (32)+TX, chloralose (127)+TX, copper naphthenate [CCN]+TX,copper oxychloride (171)+TX, diazinon (227)+TX, dicyclopentadiene(chemical name) (1069)+TX, guazatine (422)+TX, guazatine acetates(422)+TX, methiocarb (530)+TX, pyridin-4-amine (IUPAC name) (23)+TX,thiram (804)+TX, trimethacarb (840)+TX, zinc naphthenate [CCN] and ziram(856)+TX, a virucide selected from the group of substances consisting ofimanin (alternative name) [CCN] and ribavirin (alternative name)[CCN]+TX,a wound protectant selected from the group of substances consisting ofmercuric oxide (512)+TX, octhilinone (590) and thiophanate-methyl(802)+TX,and biologically active compounds selected from the group consisting ofazaconazole (60207-31-0]+TX, bitertanol [70585-36-3]+TX, bromuconazole[116255-48-2]+TX, cyproconazole [94361-06-5]+TX, difenoconazole[119446-68-3]+TX, diniconazole [83657-24-3]+TX, epoxiconazole[106325-08-0]+TX, fenbuconazole [114369-43-6]+TX, fluquinconazole[136426-54-5]+TX, flusilazole [85509-19-9]+TX, flutriafol[76674-21-0]+TX, hexaconazole [79983-71-4]+TX, imazalil [35554-44-0]+TX,imibenconazole [86598-92-7]+TX, ipconazole [125225-28-7]+TX, metconazole[125116-23-6]+TX, myclobutanil [88671-89-0]+TX, pefurazoate[101903-30-4]+TX, penconazole [66246-88-6]+TX, prothioconazole[178928-70-6]+TX, pyrifenox [88283-41-4]+TX, prochloraz [67747-09-5]+TX,propiconazole [60207-90-1]+TX, simeconazole [149508-90-7]+TX,tebucon-azole [107534-96-3]+TX, tetraconazole [112281-77-3]+TX,triadimefon [43121-43-3]+TX, triadimenol [55219-65-3]+TX, triflumizole[99387-89-0]+TX, triticonazole [131983-72-7]+TX, ancymidol[12771-68-5]+TX, fenarimol [60168-88-9]+TX, nuarimol [63284-71-9]+TX,bupirimate [41483-43-6]+TX, dimethirimol [5221-53-4]+TX, ethirimol[23947-60-6]+TX, dodemorph [1593-77-7]+TX, fenpropidine [67306-00-7]+TX,fenpropimorph [67564-91-4]+TX, spiroxamine [118134-30-8]+TX, tridemorph[81412-43-3]+TX, cyprodinil [121552-61-2]+TX, mepanipyrim[110235-47-7]+TX, pyrimethanil [53112-28-0]+TX, fenpiclonil[74738-17-3]+TX, fludioxonil [131341-86-1]+TX, benalaxyl[71626-11-4]+TX, furalaxyl [57646-30-7]+TX, metalaxyl [57837-19-1]+TX,R-metalaxyl [70630-17-0]+TX, ofurace [58810-48-3]+TX, oxadixyl[77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX,debacarb [62732-91-6]+TX, fuberidazole [3878-19-1]+TX, thiabendazole[148-79-8]+TX, chlozolinate [84332-86-5]+TX, dichlozoline[24201-58-9]+TX, iprodione [36734-19-7]+TX, myclozoline [54864-61-8]+TX,procymidone [32809-16-8]+TX, vinclozoline [50471-44-8]+TX, boscalid[188425-85-6]+TX, carboxin [5234-68-4]+TX, fenfuram [24691-80-3]+TX,flutolanil [66332-96-5]+TX, mepronil [55814-41-0]+TX, oxycarboxin[5259-88-1]+TX, penthiopyrad [183675-82-3]+TX, thifluzamide[130000-40-7]+TX, guazatine [108173-90-6]+TX, dodine [2439-10-3][112-65-2] (free base)+TX, iminoctadine [13516-27-3]+TX, azoxystrobin[131860-33-8]+TX, dimoxystrobin [149961-52-4]+TX, enestroburin {Proc.BCPC, Int. Congr., Glasgow, 2003, 1, 93}+TX, fluoxastrobin[361377-29-9]+TX, kresoxim-methyl [143390-89-0]+TX, metominostrobin[133408-50-1]+TX, trifloxystrobin [141517-21-7]+TX, orysastrobin[248593-16-0]+TX, picoxystrobin [117428-22-5]+TX, pyraclostrobin[175013-18-0]+TX, ferbam [14484-64-1]+TX, mancozeb [8018-01-7]+TX, maneb[12427-38-2]+TX, metiram [9006-42-2]+TX, propineb [12071-83-9]+TX,thiram [137-26-8]+TX, zineb [12122-67-7]+TX, ziram [137-30-4]+TX,captafol [2425-06-1]+TX, captan [133-06-2]+TX, dichlofluanid[1085-98-9]+TX, fluoroimide [41205-21-4]+TX, folpet [133-07-3]+TX,tolylfluanid [731-27-1]+TX, bordeaux mixture [8011-63-0]+TX,copperhydroxid [20427-59-2]+TX, copperoxychlorid [1332-40-7]+TX,coppersulfat [7758-98-7]+TX, copperoxid [1317-39-1]+TX, mancopper[53988-93-5]+TX, oxine-copper [10380-28-6]+TX, dinocap [131-72-6]+TX,nitrothal-isopropyl [10552-74-6]+TX, edifenphos [17109-49-8]+TX,iprobenphos [26087-47-8]+TX, isoprothiolane [50512-35-1]+TX, phosdiphen[36519-00-3]+TX, pyrazophos [13457-18-6]+TX, tolclofos-methyl[57018-04-9]+TX, acibenzolar-S-methyl [135158-54-2]+TX, anilazine[101-05-3]+TX, benthiavalicarb [413615-35-7]+TX, blasticidin-S[2079-00-7]+TX, chinomethionat [2439-01-2]+TX, chloroneb [2675-77-6]+TX,chlorothalonil [1897-45-6]+TX, cyflufenamid [180409-60-3]+TX, cymoxanil[57966-95-7]+TX, dichlone [117-80-6]+TX, diclocymet [139920-32-4]+TX,diclomezine [62865-36-5]+TX, dicloran [99-30-9]+TX, diethofencarb[87130-20-9]+TX, dimetho-morph [110488-70-5]+TX, SYP-LI90 (Flumorph)[211867-47-9]+TX, dithianon [3347-22-6]+TX, ethaboxam [162650-77-3]+TX,etridiazole [2593-15-9]+TX, famoxadone [131807-57-3]+TX, fenamidone[161326-34-7]+TX, fenoxanil [115852-48-7]+TX, fentin [668-34-8]+TX,ferimzone [89269-64-7]+TX, fluazinam [79622-59-6]+TX, fluopicolide[239110-15-7]+TX, flusulfamide [106917-52-6]+TX, fenhexamid[126833-17-8]+TX, fosetyl-aluminium [39148-24-8]+TX, hymexazol[10004-44-1]+TX, iprovalicarb [140923-17-7]+TX, IKF-916 (Cyazofamid)[120116-88-3]+TX, kasugamycin [6980-18-3]+TX, methasulfocarb[66952-49-6]+TX, metrafenone [220899-03-6]+TX, pencycuron[66063-05-6]+TX, phthalide [27355-22-2]+TX, polyoxins [11113-80-7]+TX,probenazole [27605-76-1]+TX, propamocarb [25606-41-1]+TX, proquinazid[189278-12-4]+TX, pyroquilon [57369-32-1]+TX, quinoxyfen[124495-18-7]+TX, quintozene [82-68-8]+TX, sulfur [7704-34-9]+TX,tiadinil [223580-51-6]+TX, triazoxide [72459-58-6]+TX, tricyclazole[41814-78-2]+TX, triforine [26644-46-2]+TX, validamycin [37248-47-8]+TX,zoxamide (RH7281) [156052-68-5]+TX, mandipropamid [374726-62-2]+TX,isopyrazam [881685-58-1]+TX, sedaxane [874967-67-6]+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide(dislosed in WO 2007/048556)+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(3′,4′,5′-trifluoro-biphenyl-2-yl)-amide (disclosed in WO2006/087343)+TX,[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11Hnaphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl-cyclopropanecarboxylate[915972-17-7]+TX,1,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1H-pyrazole-4-carboxamide[926914-55-8]+TX; lancotrione [1486617-21-3]+TX, florpyrauxifen[943832-81-3]+TX, ipfentrifluconazole[1417782-08-1]+TX,mefentrifluconazole [1417782-03-6]+TX, quinofumelin [861647-84-9]+TX,chloroprallethrin [399572-87-3]+TX, cyhalodiamide [1262605-53-7]+TX,fluazaindolizine [1254304-22-7]+TX, fluxametamide [928783-29-3]+TX,epsilon-metofluthrin [240494-71-7]+TX, epsilon-momfluorothrin[1065124-65-3]+TX, pydiflumetofen [1228284-64-7]+TX, kappa-bifenthrin[439680-76-9]+TX, broflanilide [1207727-04-5]+TX, dicloromezotiaz[1263629-39-5]+TX, dipymetitrone [16114-35-5]+TX, pyraziflumid[942515-63-1]+TX, kappa-tefluthrin [391634-71-2]+TX, fenpicoxamid[517875-34-2]+TX; fluindapyr [1383809-87-7]+TX; alpha-bromadiolone[28772-56-7]+TX; flupyrimin [1689566-03-7]+TX; benzpyrimoxan[1449021-97-9]+TX; acynonapyr [1332838-17-1]+TX; inpyrfluxam[1352994-67-2]+TX, isoflucypram [1255734-28-1]+TX; rescalure[64309-03-1]+TX; aminopyrifen [1531626-08-0]+TX; tyclopyrazoflor[1477919-27-9]+TX; and spiropidion [1229023-00-0]+TX; and microbialsincluding: Acinetobacter lwoffii+TX, Acremonium alternatum+TX+TX,Acremonium cephalosporium+TX+TX, Acremonium diospyri+TX, Acremoniumobclavatum+TX, Adoxophyes orana granulovirus (AdoxGV) (Capex®)+TX,Agrobacterium radiobacter strain K84 (Galltrol-A®)+TX, Alternariaalternate+TX, Alternaria cassia+TX, Alternaria destruens (Smolder®)+TX,Ampelomyces quisqualis (AQ10®)+TX, Aspergillus flavus AF36 (AF36®)+TX,Aspergillus flavus NRRL 21882 (Aflaguard®)+TX, Aspergillus spp.+TX,Aureobasidium pullulans+TX, Azospirillum+TX, (MicroAZ®+TX, TAZO B®)+TX,Azotobacter+TX, Azotobacter chroocuccum (Azotomeal®)+TX, Azotobactercysts (Bionatural Blooming Blossoms®)+TX, Bacillus amyloliquefaciens+TX,Bacillus cereus+TX, Bacillus chitinosporus strain CM-1+TX, Bacilluschitinosporus strain AQ746+TX, Bacillus licheniformis strain HB-2(Biostart™ Rhizoboost®)+TX, Bacillus licheniformis strain 3086(EcoGuard®+TX, Green Releaf®)+TX, Bacillus circulans+TX, Bacillus firmus(BioSafe®+TX, BioNem-WP®+TX, VOTiVO®)+TX, Bacillus firmus strainI-1582+TX, Bacillus macerans+TX, Bacillus marismortui+TX, Bacillusmegaterium+TX, Bacillus mycoides strain AQ726+TX, Bacillus papillae(Milky Spore Powder®)+TX, Bacillus pumilus spp.+TX, Bacillus pumilusstrain GB34 (Yield Shield®)+TX, Bacillus pumilus strain AQ717+TX,Bacillus pumilus strain QST 2808 (Sonata®+TX, Ballad Plus®)+TX, Bacillusspahericus (VectoLex®)+TX, Bacillus spp.+TX, Bacillus spp. strainAQ175+TX, Bacillus spp. strain AQ177+TX, Bacillus spp. strain AQ178+TX,Bacillus subtilis strain QST 713 (CEASE®+TX, Serenade®+TX,Rhapsody®)+TX, Bacillus subtilis strain QST 714 (JAZZ®)+TX, Bacillussubtilis strain AQ153+TX, Bacillus subtilis strain AQ743+TX, Bacillussubtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX,Bacillus subtilis var. amyloliquefaciens strain FZB24 (Taegro®+TX,Rhizopro®)+TX, Bacillus thuringiensis Cry 2Ae+TX, Bacillus thuringiensisCrylAb+TX, Bacillus thuringiensis aizawai GC 91 (Agree®)+TX, Bacillusthuringiensis israelensis (BMP123®+TX, Aquabac®+TX, VectoBac®)+TX,Bacillus thuringiensis kurstaki (Javelin®+TX, Deliver®+TX, CryMax®+TX,Bonide®+TX, Scutella WP®+TX, Turilav WP®+TX, Astuto®+TX, Dipel WP®+TX,Biobit®+TX, Foray®)+TX, Bacillus thuringiensis kurstaki BMP 123(Baritone®)+TX, Bacillus thuringiensis kurstaki HD-1(Bioprotec-CAF/3P®)+TX, Bacillus thuringiensis strain BD #32+TX,Bacillus thuringiensis strain AQ52+TX, Bacillus thuringiensis var.aizawai (XenTari®+TX, DiPel®)+TX, bacteria spp. (GROWMEND®+TX,GROWSWEET®+TX, Shootup®)+TX, bacteriophage of Clavipacter michiganensis(AgriPhage®)+TX, Bakflor®+TX, Beauveria bassiana (Beaugenic®+TX,Brocaril WP®)+TX, Beauveria bassiana GHA (Mycotrol ES®+TX, MycotrolO®+TX, BotaniGuard®)+TX, Beauveria brongniartii (Engerlingspilz®+TX,Schweizer Beauveria®+TX, Melocont®)+TX, Beauveria spp.+TX, Botrytiscineria+TX, Bradyrhizobium japonicum (TerraMax®)+TX, Brevibacillusbrevis+TX, Bacillus thuringiensis tenebrionis (Novodor®)+TX,BtBooster+TX, Burkholderia cepacia (Deny®+TX, Intercept®+TX, BlueCircle®)+TX, Burkholderia gladii+TX, Burkholderia gladioli+TX,Burkholderia spp.+TX, Canadian thistle fungus (CBH CanadianBioherbicide®)+TX, Candida butyri+TX, Candida famata+TX, Candidafructus+TX, Candida glabrata+TX, Candida guilliermondii+TX, Candidamelibiosica+TX, Candida oleophila strain O+TX, Candida parapsilosis+TX,Candida pelliculosa+TX, Candida pulcherrima+TX, Candida reukaufii+TX,Candida saitoana (Bio-Coat®+TX, Biocure®)+TX, Candida sake+TX, Candidaspp.+TX, Candida tenius+TX, Cedecea dravisae+TX, Cellulomonasflavigena+TX, Chaetomium cochliodes (Nova-Cide®)+TX, Chaetomium globosum(Nova-Cide®)+TX, Chromobacterium subtsugae strain PRAA4-1T(Grandevo®)+TX, Cladosporium cladosporioides+TX, Cladosporiumoxysporum+TX, Cladosporium chlorocephalum+TX, Cladosporium spp.+TX,Cladosporium tenuissimum+TX, Clonostachys rosea (EndoFine®)+TX,Colletotrichum acutatum+TX, Coniothyrium minitans (Cotans WG®)+TX,Coniothyrium spp.+TX, Cryptococcus albidus (YIELDPLUS®)+TX, Cryptococcushumicola+TX, Cryptococcus infirmo-miniatus+TX, Cryptococcuslaurentii+TX, Cryptophlebia leucotreta granulovirus (Cryptex®)+TX,Cupriavidus campinensis+TX, Cydia pomonella granulovirus (CYD-X®)+TX,Cydia pomonella granulovirus (Madex®+TX, Madex Plus®+TX, MadexMax/Carpovirusine®)+TX, Cylindrobasidium laeve (Stumpout®)+TX,Cylindrocladium+TX, Debaryomyces hansenii+TX, Drechslerahawaiinensis+TX, Enterobacter cloacae+TX, Enterobacteriaceae+TX,Entomophtora virulenta (Vektor®)+TX, Epicoccum nigrum+TX, Epicoccumpurpurascens+TX, Epicoccum spp.+TX, Filobasidium floriforme+TX, Fusariumacuminatum+TX, Fusarium chlamydosporum+TX, Fusarium oxysporum(Fusaclean®/Biofox C®)+TX, Fusarium proliferatum+TX, Fusarium spp.+TX,Galactomyces geotrichum+TX, Gliocladium catenulatum (Primastop®+TX,Prestop®)+TX, Gliocladium roseum+TX, Gliocladium spp. (SoilGard®)+TX,Gliocladium virens (Soilgard®)+TX, Granulovirus (Granupom®)+TX,Halobacillus halophilus+TX, Halobacillus litoralis+TX, Halobacillustrueperi+TX, Halomonas spp.+TX, Halomonas subglaciescola+TX, Halovibriovariabilis+TX, Hanseniaspora uvarum+TX, Helicoverpa armigeranucleopolyhedrovirus (Helicovex®)+TX, Helicoverpa zea nuclearpolyhedrosis virus (Gemstar®)+TX, Isoflavone—formononetin(Myconate®)+TX, Kloeckera apiculata+TX, Kloeckera spp.+TX, Lagenidiumgiganteum (Laginex®)+TX, Lecanicillium longisporum (Vertiblast®)+TX,Lecanicillium muscarium (Vertikil®)+TX, Lymantria Disparnucleopolyhedrosis virus (Disparvirus®)+TX, Marinococcus halophilus+TX,Meira geulakonigii+TX, Metarhizium anisopliae (Met52®)+TX, Metarhiziumanisopliae (Destruxin WP®)+TX, Metschnikowia fruticola (Shemer®)+TX,Metschnikowia pulcherrima+TX, Microdochium dimerum (Antibot®)+TX,Micromonospora coerulea+TX, Microsphaeropsis ochracea+TX, Muscodor albus620 (Muscudor®)+TX, Muscodor roseus strain A3-5+TX, Mycorrhizae spp.(AMykor®+TX, Root Maximizer®)+TX, Myrothecium verrucaria strainAARC-0255 (DiTera®)+TX, BROS PLUS®+TX, Ophiostoma piliferum strain D97(Sylvanex®)+TX, Paecilomyces farinosus+TX, Paecilomyces fumosoroseus(PFR-97®+TX, PreFeRal®)+TX, Paecilomyces linacinus (Biostat WP®)+TX,Paecilomyces lilacinus strain 251 (MeloCon WG®)+TX, Paenibacilluspolymyxa+TX, Pantoea agglomerans (BlightBan C9-1®)+TX, Pantoea spp.+TX,Pasteuria spp. (Econem®)+TX, Pasteuria nishizawae+TX, Penicilliumaurantiogriseum+TX, Penicillium billai (Jumpstart®+TX, TagTeam®)+TX,Penicillium brevicompactum+TX, Penicillium frequentans+TX, Penicilliumgriseofulvum+TX, Penicillium purpurogenum+TX, Penicillium spp.+TX,Penicillium viridicatum+TX, Phlebiopsis gigantean (Rotstop®)+TX,phosphate solubilizing bacteria (Phosphomeal®)+TX, Phytophthoracryptogea+TX, Phytophthora palmivora (Devine®)+TX, Pichia anomala+TX,Pichia guilermondii+TX, Pichia membranaefaciens+TX, Pichia onychis+TX,Pichia stipites+TX, Pseudomonas aeruginosa+TX, Pseudomonas aureofasciens(Spot-Less Biofungicide®)+TX, Pseudomonas cepacia+TX, Pseudomonaschlororaphis (AtEze®)+TX, Pseudomonas corrugate+TX, Pseudomonasfluorescens strain A506 (BlightBan A506®)+TX, Pseudomonas putida+TX,Pseudomonas reactans+TX, Pseudomonas spp.+TX, Pseudomonas syringae(Bio-Save®)+TX, Pseudomonas viridiflava+TX, Pseudomonas fluorescens(Zequanox®)+TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L®)+TX,Puccinia canaliculata+TX, Puccinia thlaspeos (Wood Warrior®)+TX, Pythiumparoecandrum+TX, Pythium oligandrum (Polygandron®+TX, Polyversum®)+TX,Pythium periplocum+TX, Rhanella aquatilis+TX, Rhanella spp.+TX, Rhizobia(Dormal®+TX, Vault®)+TX, Rhizoctonia+TX, Rhodococcus globerulus strainAQ719+TX, Rhodosporidium diobovatum+TX, Rhodosporidium toruloides+TX,Rhodotorula spp.+TX, Rhodotorula glutinis+TX, Rhodotorula graminis+TX,Rhodotorula mucilagnosa+TX, Rhodotorula rubra+TX, Saccharomycescerevisiae+TX, Salinococcus roseus+TX, Sclerotinia minor+TX, Sclerotiniaminor (SARRITOR®)+TX, Scytalidium spp.+TX, Scytalidium uredinicola+TX,Spodoptera exigua nuclear polyhedrosis virus (Spod-X®+TX, Spexit®)+TX,Serratia marcescens+TX, Serratia plymuthica+TX, Serratia spp.+TX,Sordaria fimicola+TX, Spodoptera littoralis nucleopolyhedrovirus(Littovir®)+TX, Sporobolomyces roseus+TX, Stenotrophomonasmaltophilia+TX, Streptomyces ahygroscopicus+TX, Streptomycesalbaduncus+TX, Streptomyces exfoliates+TX, Streptomyces galbus+TX,Streptomyces griseoplanus+TX, Streptomyces griseoviridis (Mycostop®)+TX,Streptomyces lydicus (Actinovate®)+TX, Streptomyces lydicus WYEC-108(ActinoGrow®)+TX, Streptomyces violaceus+TX, Tilletiopsis minor+TX,Tilletiopsis spp.+TX, Trichoderma asperellum (T34 Biocontrol®)+TX,Trichoderma gamsii (Tenet®)+TX, Trichoderma atroviride (Plantmate®)+TX,Trichoderma hamatum TH 382+TX, Trichoderma harzianum rifai(Mycostar®)+TX, Trichoderma harzianum T-22 (Trianum-P®+TX, PlantShieldHC®+TX, RootShield®+TX, Trianum-G®)+TX, Trichoderma harzianum T-39(Trichodex®)+TX, Trichoderma inhamatum+TX, Trichoderma koningii+TX,Trichoderma spp. LC 52 (Sentinel®)+TX, Trichoderma lignorum+TX,Trichoderma longibrachiatum+TX, Trichoderma polysporum (Binab T®)+TX,Trichoderma taxi+TX, Trichoderma virens+TX, Trichoderma virens (formerlyGliocladium virens GL-21) (SoilGuard®)+TX, Trichoderma viride+TX,Trichoderma viride strain ICC 080 (Remedier®)+TX, Trichosporonpullulans+TX, Trichosporon spp.+TX, Trichothecium spp.+TX, Trichotheciumroseum+TX, Typhula phacorrhiza strain 94670+TX, Typhula phacorrhizastrain 94671+TX, Ulocladium atrum+TX, Ulocladium oudemansii(Botry-Zen®)+TX, Ustilago maydis+TX, various bacteria and supplementarymicronutrients (Natural II®)+TX, various fungi (MillenniumMicrobes®)+TX, Verticillium chlamydosporium+TX, Verticillium lecanii(Mycotal®+TX, Vertalec®)+TX, Vip3Aa20 (VIPtera®)+TX, Virgibaclillusmarismortui+TX, Xanthomonas campestris pv. Poae (Camperico®)+TX,Xenorhabdus bovienii+TX, Xenorhabdus nematophilus; and Plant extractsincluding: pine oil (Retenol®)+TX, azadirachtin (Plasma Neem Oil®+TX,AzaGuard®+TX, MeemAzal®+TX, Molt-X®+TX, Botanical IGR (Neemazad®+TX,Neemix®)+TX, canola oil (Lilly Miller Vegol®)+TX, Chenopodiumambrosioides near ambrosioides (Requiem®)+TX, Chrysanthemum extract(Crisant®)+TX, extract of neem oil (Trilogy®)+TX, essentials oils ofLabiatae (Botania®)+TX, extracts of clove rosemary peppermint and thymeoil (Garden Insect Killer®)+TX, Glycinebetaine (Greenstim®)+TX,garlic+TX, lemongrass oil (GreenMatch®)+TX, neem oil+TX, Nepeta cataria(Catnip oil)+TX, Nepeta catarina+TX, nicotine+TX, oregano oil(MossBuster®)+TX, Pedaliaceae oil (Nematon®)+TX, pyrethrum+TX, Quillajasaponaria (NemaQ®)+TX, Reynoutria sachalinensis (Regalia®+TX,Sakalia®)+TX, rotenone (Eco Roten®)+TX, Rutaceae plant extract(Soleo®)+TX, soybean oil (Ortho Ecosense®)+TX, tea tree oil (TimorexGold®)+TX, thymus oil+TX, AGNIQUE® MMF+TX, BugOil®+TX, mixture ofrosemary sesame pepermint thyme and cinnamon extracts (EF 300®)+TX,mixture of clove rosemary and peppermint extract (EF 400®)+TX, mixtureof clove pepermint garlic oil and mint (Soil Shot®)+TX, kaolin(Screen®)+TX, storage glucam of brown algae (Laminarin®); and pheromonesincluding: blackheaded fireworm pheromone (3M Sprayable BlackheadedFireworm Pheromone®)+TX, Codling Moth Pheromone (Paramountdispenser-(CM)/Isomate C-Plus®)+TX, Grape Berry Moth Pheromone (3MMEC-GBM Sprayable Pheromone®)+TX, Leafroller pheromone (3M MEC—LRSprayable Pheromone®)+TX, Muscamone (Snip7 Fly Bait®+TX, Starbar PremiumFly Bait®)+TX, Oriental Fruit Moth Pheromone (3M oriental fruit mothsprayable Pheromone®)+TX, Peachtree Borer Pheromone (Isomate-P®)+TX,Tomato Pinworm Pheromone (3M Sprayable Pheromone®)+TX, Entostat powder(extract from palm tree) (Exosex CM®)+TX, (E+TX,Z+TX,Z)-3+TX,8+TX,11Tetradecatrienyl acetate+TX,(Z+TX,Z+TX,E)-7+TX,11+TX,13-Hexadecatrienal+TX,(E+TX,Z)-7+TX,9-Dodecadien-1-yl acetate+TX, 2-Methyl-1-butanol+TX,Calcium acetate+TX, Scenturion®+TX, Biolure®+TX, Check-Mate®+TX,Lavandulyl senecioate; andMacrobials including: Aphelinus abdominalis+TX, Aphidius ervi(Aphelinus-System®)+TX, Acerophagus papaya+TX, Adalia bipunctata(Adalia-System®)+TX, Adalia bipunctata (Adaline®)+TX, Adalia bipunctata(Aphidalia®)+TX, Ageniaspis citricola+TX, Ageniaspis fuscicollis+TX,Amblyseius andersoni (Anderline®+TX, Andersoni-System®)+TX, Amblyseiuscalifornicus (Amblyline®+TX, Spical®)+TX, Amblyseius cucumeris(Thripex®+TX, Bugline cucumeris®)+TX, Amblyseius fallacis(Fallacis®)+TX, Amblyseius swirskii (Bugline swirskii®+TX,Swirskii-Mite®)+TX, Amblyseius womersleyi (WomerMite®)+TX, Amitushesperidum+TX, Anagrus atomus+TX, Anagyrus fusciventris+TX, Anagyruskamali+TX, Anagyrus loecki+TX, Anagyrus pseudococci (Citripar®)+TX,Anicetus benefices+TX, Anisopteromalus calandrae+TX, Anthocorisnemoralis (Anthocoris-System®)+TX, Aphelinus abdominalis (Apheline®+TX,Aphiline®)+TX, Aphelinus asychis+TX, Aphidius colemani (Aphipar®)+TX,Aphidius ervi (Ervipar®)+TX, Aphidius gifuensis+TX, Aphidius matricariae(Aphipar-M®)+TX, Aphidoletes aphidimyza (Aphidend®)+TX, Aphidoletesaphidimyza (Aphidoline®)+TX, Aphytis lingnanensis+TX, Aphytismelinus+TX, Aprostocetus hagenowii+TX, Atheta coriaria (Staphyline®)+TX,Bombus spp.+TX, Bombus terrestris (Natupol Beehive®)+TX, Bombusterrestris (Beeline®+TX, Tripol®)+TX, Cephalonomia stephanoderis+TX,Chilocorus nigritus+TX, Chrysoperla carnea (Chrysoline®)+TX, Chrysoperlacarnea (Chrysopa®)+TX, Chrysoperla rufilabris+TX, Cirrospilusingenuus+TX, Cirrospilus quadristriatus+TX, Citrostichusphyllocnistoides+TX, Closterocerus chamaeleon+TX, Closterocerus spp.+TX,Coccidoxenoides perminutus (Planopar®)+TX, Coccophagus cowperi+TX,Coccophagus lycimnia+TX, Cotesia flavipes+TX, Cotesia plutellae+TX,Cryptolaemus montrouzieri (Cryptobug®+TX, Cryptoline®)+TX, Cybocephalusnipponicus+TX, Dacnusa sibirica+TX, Dacnusa sibirica (Minusa®)+TX,Diglyphus isaea (Diminex®)+TX, Delphastus catalinae (Delphastus®)+TX,Delphastus pusillus+TX, Diachasmimorpha krausii+TX, Diachasmimorphalongicaudata+TX, Diaparsis jucunda+TX, Diaphorencyrtus aligarhensis+TX,Diglyphus isaea+TX, Diglyphus isaea (Miglyphus®+TX, Digline®)+TX,Dacnusa sibirica (DacDigline®+TX, Minex®)+TX, Diversinervus spp.+TX,Encarsia citrina+TX, Encarsia formosa (Encarsia Max®+TX, Encarline®+TX,En-Strip®)+TX, Eretmocerus eremicus (Enermix®)+TX, Encarsiaguadeloupae+TX, Encarsia haitiensis+TX, Episyrphus balteatus(Syrphidend®)+TX, Eretmoceris siphonini+TX, Eretmocerus californicus+TX,Eretmocerus eremicus (Ercal®+TX, Eretline E®)+TX, Eretmocerus eremicus(Bemimix®)+TX, Eretmocerus hayati+TX, Eretmocerus mundus (Bemipar®+TX,Eretline M®)+TX, Eretmocerus siphonini+TX, Exochomusquadripustulatus+TX, Feltiella acarisuga (Spidend®)+TX, Feltiellaacarisuga (Feltiline®)+TX, Fopius arisanus+TX, Fopius ceratitivorus+TX,Formononetin (Wirless Beehome®)+TX, Franklinothrips vespiformis(Vespop®)+TX, Galendromus occidentalis+TX, Goniozus legneri+TX,Habrobracon hebetor+TX, Harmonia axyridis (HarmoBeetle®)+TX,Heterorhabditis spp. (Lawn Patrol®)+TX, Heterorhabditis bacteriophora(NemaShield HB®+TX, Nemaseek®+TX, Terranem-Nam®+TX, Terranem®+TX,Larvanem®+TX, B-Green®+TX, NemAttack®+TX, Nematop®)+TX, Heterorhabditismegidis (Nemasys H®+TX, BioNem H®+TX, Exhibitline Hm®+TX,Larvanem-M®)+TX, Hippodamia convergens+TX, Hypoaspis aculeifer(Aculeifer-System®+TX, Entomite-A®)+TX, Hypoaspis miles (Hypoline M®+TX,Entomite-M®)+TX, Lbalia leucospoides+TX, Lecanoideus floccissimus+TX,Lemophagus errabundus+TX, Leptomastidea abnormis+TX, Leptomastixdactylopii (Leptopar®)+TX, Leptomastix epona+TX, Lindorus lophanthae+TX,Lipolexis oregmae+TX, Lucilia caesar (Natufly®)+TX, Lysiphlebustestaceipes+TX, Macrolophus caliginosus (Mirical-N®+TX, Macroline C®+TX,Mirical®)+TX, Mesoseiulus longipes+TX, Metaphycus flavus+TX, Metaphycuslounsburyi+TX, Micromus angulatus (Milacewing®)+TX, Microterysflavus+TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar®)+TX,Neodryinus typhlocybae+TX, Neoseiulus californicus+TX, Neoseiuluscucumeris (THRYPEX®)+TX, Neoseiulus fallacis+TX, Nesideocoris tenuis(NesidioBug®+TX, Nesibug®)+TX, Ophyra aenescens (Biofly®)+TX, Oriusinsidiosus (Thripor-I®+TX, Oriline I®)+TX, Orius laevigatus(Thripor-L®+TX, Oriline I®)+TX, Orius majusculus (Oriline M®)+TX, Oriusstrigicollis (Thripor-S®)+TX, Pauesia juniperorum+TX, Pediobiusfoveolatus+TX, Phasmarhabditis hermaphrodita (Nemaslug®)+TX,Phymastichus coffea+TX, Phytoseiulus macropilus+TX, Phytoseiuluspersimilis (Spidex®+TX, Phytoline P®)+TX, Podisus maculiventris(Podisus®)+TX, Pseudacteon curvatus+TX, Pseudacteon obtusus+TX,Pseudacteon tricuspis+TX, Pseudaphycus maculipennis+TX, Pseudleptomastixmexicana+TX, Psyllaephagus pilosus+TX, Psyttalia concolor (complex)+TX,Quadrastichus spp.+TX, Rhyzobius lophanthae+TX, Rodolia cardinalis+TX,Rumina decollate+TX, Semielacher petiolatus+TX, Sitobion avenae(Ervibank®)+TX, Steinernema carpocapsae (Nematac C®+TX, Millenium®+TX,BioNem C®+TX, NemAttack®+TX, Nemastar®+TX, Capsanem®)+TX, Steinernemafeltiae (NemaShield®+TX, Nemasys F®+TX, BioNem F®+TX,Steinernema-System®+TX, NemAttack®+TX, Nemaplus®+TX, Exhibitline Sf®+TX,Scia-Rid®+TX, Entonem®)+TX, Steinernema kraussei (Nemasys L®+TX, BioNemL®+TX, Exhibitline Srb®)+TX, Steinernema riobrave (BioVector®+TX,BioVektor®)+TX, Steinernema scapterisci (Nematac S®)+TX, Steinernemaspp.+TX, Steinernematid spp. (Guardian Nematodes®)+TX, Stethoruspunctillum (Stethorus®)+TX, Tamarixia radiate+TX, Tetrastichussetifer+TX, Thripobius semiluteus+TX, Torymus sinensis+TX, Trichogrammabrassicae (Tricholine B®)+TX, Trichogramma brassicae (Tricho-Strip®)+TX,Trichogramma evanescens+TX, Trichogramma minutum+TX, Trichogrammaostriniae+TX, Trichogramma platneri+TX, Trichogramma pretiosum+TX,Xanthopimpla stemmator; and other biologicals including: abscisicacid+TX, bioSea®+TX, Chondrostereum purpureum (Chontrol Paste®)+TX,Colletotrichum gloeosporioides (Collego®)+TX, Copper Octanoate(Cueva®)+TX, Delta traps (Trapline D®)+TX, Erwinia amylovora (Harpin)(ProAct®+TX, Ni-HIBIT Gold CST®)+TX, Ferri-phosphate (Ferramol®)+TX,Funnel traps (Trapline Y®)+TX, Gallex®+TX, Grower's Secret®+TX,Homo-brassonolide+TX, Iron Phosphate (Lilly Miller Worry Free FerramolSlug & Snail Bait®)+TX, MCP hail trap (Trapline F®)+TX, Microctonushyperodae+TX, Mycoleptodiscus terrestris (Des-X®)+TX, BioGain®+TX,Aminomite®+TX, Zenox®+TX, Pheromone trap (Thripline ams®)+TX, potassiumbicarbonate (MilStop®)+TX, potassium salts of fatty acids (Sanova®)+TX,potassium silicate solution (Sil-Matrix®)+TX, potassiumiodide+potassiumthiocyanate (Enzicur®)+TX, SuffOil-X®+TX, Spidervenom+TX, Nosema locustae (Semaspore Organic Grasshopper Control®)+TX,Sticky traps (Trapline YF®+TX, Rebell Amarillo®)+TX and Traps(Takitrapline y+B®)+TX.The references in brackets behind the active ingredients, e.g.[3878-19-1] refer to the Chemical Abstracts Registry number. The abovedescribed mixing partners are known. Where the active ingredients areincluded in “The Pesticide Manual” [The Pesticide Manual—A WorldCompendium; Thirteenth Edition; Editor: C. D. S. TomLin; The BritishCrop Protection Council], they are described therein under the entrynumber given in round brackets hereinabove for the particular compound;for example, the compound “abamectin” is described under entry number(1). Where “[CCN]” is added hereinabove to the particular compound, thecompound in question is included in the “Compendium of Pesticide CommonNames”, which is accessible on the internet [A. Wood; Compendium ofPesticide Common Names, Copyright @ 1995-2004]; for example, thecompound “acetoprole” is described under the internet addresshttp://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred tohereinabove by a so-called “common name”, the relevant “ISO common name”or another “common name” being used in individual cases. If thedesignation is not a “common name”, the nature of the designation usedinstead is given in round brackets for the particular compound; in thatcase, the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemicalname”, a “traditional name”, a “compound name” or a “development code”is used or, if neither one of those designations nor a “common name” isused, an “alternative name” is employed. “CAS Reg. No” means theChemical Abstracts Registry Number.

The active ingredient mixture of the compounds of formula (I) selectedfrom Table A-1 to A-100 and A with active ingredients described abovecomprises a compound selected from Table A-1 to A-100 and A and anactive ingredient as described above preferably in a mixing ratio offrom 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in aratio of from 20:1 to 1:20, even more especially from 10:1 to 1:10, veryespecially from 5:1 and 1:5, special preference being given to a ratioof from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 being likewisepreferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4,or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5,or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75,or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750,or 2:750, or 4:750. Those mixing ratios are by weight.The mixtures as described above can be used in a method for controllingpests, which comprises applying a composition comprising a mixture asdescribed above to the pests or their environment, with the exception ofa method for treatment of the human or animal body by surgery or therapyand diagnostic methods practised on the human or animal body.The mixtures comprising a compound of formula (I) selected from TableA-1 to A-100 and A and one or more active ingredients as described abovecan be applied, for example, in a single “ready-mix” form, in a combinedspray mixture composed from separate formulations of the single activeingredient components, such as a “tank-mix”, and in a combined use ofthe single active ingredients when applied in a sequential manner, i.e.one after the other with a reasonably short period, such as a few hoursor days. The order of applying the compounds of formula (I) selectedfrom Table A-1 to A-100 and A and the active ingredients as describedabove is not essential for working the present invention.The compositions according to the invention can also comprise furthersolid or liquid auxiliaries, such as stabilizers, for exampleunepoxidized or epoxidized vegetable oils (for example epoxidizedcoconut oil, rapeseed oil or soya oil), antifoams, for example siliconeoil, preservatives, viscosity regulators, binders and/or tackifiers,fertilizers or other active ingredients for achieving specific effects,for example bactericides, fungicides, nematocides, plant activators,molluscicides or herbicides.The compositions according to the invention are prepared in a mannerknown per se, in the absence of auxiliaries for example by grinding,screening and/or compressing a solid active ingredient and in thepresence of at least one auxiliary for example by intimately mixingand/or grinding the active ingredient with the auxiliary (auxiliaries).These processes for the preparation of the compositions and the use ofthe compounds I for the preparation of these compositions are also asubject of the invention.The application methods for the compositions, that is the methods ofcontrolling pests of the abovementioned type, such as spraying,atomizing, dusting, brushing on, dressing, scattering or pouring—whichare to be selected to suit the intended aims of the prevailingcircumstances—and the use of the compositions for controlling pests ofthe abovementioned type are other subjects of the invention. Typicalrates of concentration are between 0.1 and 1000 ppm, preferably between0.1 and 500 ppm, of active ingredient. The rate of application perhectare is generally 1 to 2000 g of active ingredient per hectare, inparticular 10 to 1000 g/ha, preferably 10 to 600 g/ha.A preferred method of application in the field of crop protection isapplication to the foliage of the plants (foliar application), it beingpossible to select frequency and rate of application to match the dangerof infestation with the pest in question. Alternatively, the activeingredient can reach the plants via the root system (systemic action),by drenching the locus of the plants with a liquid composition or byincorporating the active ingredient in solid form into the locus of theplants, for example into the soil, for example in the form of granules(soil application). In the case of paddy rice crops, such granules canbe metered into the flooded paddy-field.The compounds of the invention and compositions thereof are also besuitable for the protection of plant propagation material, for exampleseeds, such as fruit, tubers or kernels, or nursery plants, againstpests of the abovementioned type. The propagation material can betreated with the compound prior to planting, for example seed can betreated prior to sowing. Alternatively, the compound can be applied toseed kernels (coating), either by soaking the kernels in a liquidcomposition or by applying a layer of a solid composition. It is alsopossible to apply the compositions when the propagation material isplanted to the site of application, for example into the seed furrowduring drilling. These treatment methods for plant propagation materialand the plant propagation material thus treated are further subjects ofthe invention. Typical treatment rates would depend on the plant andpest/fungi to be controlled and are generally between 1 to 200 grams per100 kg of seeds, preferably between 5 to 150 grams per 100 kg of seeds,such as between 10 to 100 grams per 100 kg of seeds.The term seed embraces seeds and plant propagules of all kinds includingbut not limited to true seeds, seed pieces, suckers, corns, bulbs,fruit, tubers, grains, rhizomes, cuttings, cut shoots and the like andmeans in a preferred embodiment true seeds.The present invention also comprises seeds coated or treated with orcontaining a compound of formula (I). The term “coated or treated withand/or containing” generally signifies that the active ingredient is forthe most part on the surface of the seed at the time of application,although a greater or lesser part of the ingredient may penetrate intothe seed material, depending on the method of application. When the saidseed product is (re)planted, it may absorb the active ingredient. In anembodiment, the present invention makes available a plant propagationmaterial adhered thereto with a compound of formula (I). Further, it ishereby made available, a composition comprising a plant propagationmaterial treated with a compound of formula (I).Seed treatment comprises all suitable seed treatment techniques known inthe art, such as seed dressing, seed coating, seed dusting, seed soakingand seed pelleting. The seed treatment application of the compoundformula (I) can be carried out by any known methods, such as spraying orby dusting the seeds before sowing or during the sowing/planting of theseeds.

PREPARATORY EXAMPLES

The following Examples illustrate, but do not limit, the invention.The compounds of the invention can be distinguished from known compoundsby virtue of greater efficacy at low application rates, which can beverified by the person skilled in the art using the experimentalprocedures outlined in the Examples, using lower application rates ifnecessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm,0.4 ppm, 0.2 ppm, 0.1 ppm or even at lower concentrations.“Mp” means melting point in ° C. Free radicals represent methyl groups.¹H and ¹⁹F NMR measurements were recorded on Brucker 400 MHz or 300 MHzspectrometers, chemical shifts are given in ppm relative to a TMSstandard. Spectra measured in deuterated solvents as indicated (br meansthat the following signal pattern is broad e.g. br s is a broad singlet;s=singlet; d=doublet; m=multiplet).

Example 1: Preparation of tert-butyl3-[[4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoyl]amino]azetidine-1-carboxylate

To a cold solution of tert-butyl 3-aminoazetidine-1-carboxylate (440 mg)in dichloromethane (10 mL) was added triethylamine (1 mL) under argonatmosphere. The reaction mixture was stirred for 10 min and then4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoylchloride (1 g) was slowly added at 0° C. The reaction mixture wasstirred for 2.5 h. To the obtained mixture was added an aqueous solutionof ammonium chloride (10 mL). The water phase was separated andextracted with ethyl acetate. The organic phases were combined, driedover sodium sulfate, filtered and evaporated under reduced pressure. Theobtained crude was purified by chromatography over silica gel with ethylacetate-cyclohexane mixture as an eluent (gradient from 0:1 to 1:1), togive tert-butyl3-[[4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoyl]amino]azetidine-1-carboxylate(807 mg) as foam. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.40-1.48 (m, 9H)2.48 (s, 3H) 3.71 (d, 1H) 3.83 (dd, 2H) 4.05-4.17 (m, 1H) 4.31-4.40 (m,2H) 4.74-4.86 (m, 1H) 6.22 (br d, 1H) 7.40-7.47 (m, 2H) 7.49-7.57 (m,4H). 19F NMR (377 MHz, CHLOROFORM-d) δ ppm −79.51 (s, 3 F)

Example 2: Preparation ofN-(azetidin-3-yl)-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzamide

To a solution of tert-butyl3-[[4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoyl]amino]azetidine-1-carboxylate(700 mg) in dichloromethane (4 mL) was added at 0° C. trifluoroaceticacid (947 μl). The resulting solution was stirred at room temperaturefor 2 h. The reaction mixture was diluted with ethyl acetate-tert-butylmethyl ether (1:1) and poured into a solution of sodium hydroxide (1N).The aqueous phase was extracted with ethyl acetate-tert-butyl methylether (1:1). The organic phase was washed with a solution of sodiumhydroxide (1N) and then with brine, then combined, dried, filtered andevaporated under reduced pressure to giveN-(azetidin-3-yl)-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzamide(563 mg) as a foam. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.46 (s, 3H)3.56 (dd, 2H) 3.70 (d, 1H) 3.99-4.16 (m, 3H) 4.88-5.01 (m, 1H) 6.63 (brd, 1H) 7.38-7.46 (m, 2H) 7.48-7.54 (m, 4H). 19F NMR (377 MHz,CHLOROFORM-d) δ ppm −79.49 (s, 3 F).

Example 3: Preparation of4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(1-ethylsulfonylazetidin-3-yl)-2-methyl-benzamide(A11)

To a solution ofN-(azetidin-1-ium-3-yl)-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzamide;2,2,2-trifluoroacetate (159 mg) in dichloromethane (0.81 mL) was addedtriethylamine (0.096 mL) followed by ethanesulfonyl chloride (0.031 mL).The reaction mixture was stirred at room temperature for 2 h 15. Thereaction mixture was diluted with dichloromethane and poured on water.The aqueous phase was extracted with dichloromethane. The combinedorganic phases were washed with water, brine then dried over magnesiumsulfate, filtered and evaporated under reduced pressure. The obtainedcrude was purified by chromatography over silica gel with ethylacetate-cyclohexane mixture (2:1) as an eluent to give4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(1-ethylsulfonylazetidin-3-yl)-2-methyl-benzamide(58 mg) as a solid. ¹H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.34 (t, 3H)2.45 (s, 3H) 2.97 (q, 2H) 3.71 (d, 1H) 4.01-4.03 (t, 2H) 4.09 (d, 1H)4.19 (t, 2H) 4.88-4.97 (m, 1H) 6.55 (d, 1H) 7.40-7.44 (m, 2H) 7.47-7.56(m, 4H). ¹⁹F NMR (377 MHz, CHLOROFORM-d) δ ppm −79.6 (s, 3 F).

Example 4 Preparation of7-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(1-methylsulfonylazetidin-3-yl)indane-4-carboxamide(Compound B01)

This compound was prepared using a library synthesis approach asdescribed below:

Stock Solutions Preparation:

-   -   1-methylsulfonylazetidin-3-amine (0.432 mmol) was dissolved in        2.4 mL of DMA (N,N-dimethylacetamide) to afford the Scaffold        stock solutions.    -   7-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]indane-4-carboxylic        acid (0.12 mmol) was dissolved in 0.8 mL of DMA        (N,N-dimethylacetamide) to afford the Building Blocks stock        solutions.    -   HATU (502 mg) was dissolved in 16 mL of DMA        (N,N-dimethylacetamide) to afford the Coupling agent stock        solution.

Dispension and Reaction:

The reactions were carried-out in a 96 well plate. In each well wassuccessively dispensed: 0.2 mL of the Building Block stock solution(0.03 mmol/reaction), 0.2 mL of the Scaffold stock solution (0.036mmol/reaction), 0.025 mL of diisopropylamine (0.15 mmol/reaction) and0.4 mL of the Coupling agent stock solution (0.033 mmol/reaction). Thewell plate was stirred at room temperature overnight then every reactionmixture was mixed with 0.1 ml of methanol before being purified bypreparative reverse phase HPLC, to give the desired compound7-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(1-methylsulfonylazetidin-3-yl)indane-4-carboxamide(compound B01). UPLC/MS: 1.98 min (retention time), 594.09 (M+H)+ massmeasured

Description of the UPLC Method Used:

Spectra were recorded on a Mass Spectrometer (ACQUITY UPLC) from Waters(SQD, SQDII Single quadrupole mass spectrometer) equipped with anelectrospray source (Polarity: positive or negative ions, Capillary: 3.0kV, Cone: 30V, Extractor: 3.00 V, Source Temperature: 150° C.,Desolvation Temperature: 400° C., Cone Gas Flow: 60 L/hr, DesolvationGas Flow: 700 L/hr, Mass range: 140 to 800 Da), DAD Wavelength range(nm): 210 to 400, and an Acquity UPLC from Waters: Solvent degasser,binary pump, heated column compartment and diode-array detector. Column:Waters UPLC HSS T3, 1.8 μm, 30×2.1 mm, Temp: 60° C., DAD Wavelengthrange (nm): 210 to 500, Solvent Gradient: A=Water/Methanol 9:1, 0.1%formic acid, B=Acetonitrile+0.1% formic acid, gradient: 0-100% B in 2.5min; Flow (ml/min) 0.75.The other compounds were prepared in a similar manner.

TABLE A Compounds of formula AA (AA)

Compound number A₁ A₂ A₃ A₄ R² A01 Cl C—F Cl CH₃ CH₃ A02 Cl C—H Cl CH₃CH₃ A03 Cl C—F Cl CH₃ CH₂Cl A04 Cl C—F Cl CH₃ CH(CH₃)₂ A05 Cl C—F Cl CH₃CH₂CH₃ A06 Cl C—F Cl CH₃ CH₂CF₃ A07 Cl C—Cl Cl CH₃ CH₃ A08 Cl C—H Cl CH₃CH₂F A09 Cl C—H Cl CH₃ CF₃ A10 Cl C—Cl Cl CH₃ CF₃ A11 Cl C—H Cl CH₃CH₂CH₃ A12 Cl C—F Cl CH₃ CHF₂ A13 Cl C—Cl Cl CH₃ CH₂CH₃ A14 Cl C—Cl ClCH₃ CHF₂ A15 Cl C—F Cl CH₃ CF₃ A16 Cl C—Cl Cl CH₃ CH₂F A17 Cl C—H CF₃CH₃ CH₂F A18 Cl C—H CF₃ CH₃ CH₂CH₃ A19 Cl C—H CF₃ CH₃ CH₃ A20 Cl C—F ClCH₃ CH₂F A21 Cl C—H Cl CH₃ CHF₂ A22 Cl C—H CF₃ CH₃ CHF₂ A23 Cl C—Cl ClCH₃ CH₂CH₂CF₃ A24 Cl C—F Cl CH₃ CH₂CH₂CF₃ A25 Cl C—Cl Cl CH₃ CH₂CF₃ A26Cl C—Cl Cl CH₃ CH₂Cl A27 Cl C—Cl Cl CH₃ CH₂Br A28 Cl C—F Cl CH₃ CH₂Br

TABLE A DATA: NMR data of Compounds of formula AA as described in TableA: Compound Number 1H NMR 19F NMR A01 1H NMR (400 MHz, CDCl3) δ ppm 2.46(s, 3 H) 19F NMR (377 MHz, 2.92 (s, 3 H) 3.71 (d, 1 H) 3.98-4.14 (m, 3H) 4.23 (t, 2 H) CDCl3) δ ppm −113.44 (s, 1 4.81-4.93 (m, 1 H) 6.40 (brd, 1 H) 7.40-7.45 (m, 1 F) −79.58 (s, 3 F) H) 7.47-7.55 (m, 2 H) 7.60(d, 2 H) A02 1H NMR (400 MHz, CDCl3) δ ppm 2.40 (s, 3 H) 19F NMR (377MHz, 2.86 (s, 3 H) 3.63 (br d, 1 H) 3.90-4.07 (m, 3 H) 4.17 (t, 2 CDCl3)δ ppm −79.50 (s, 3 H) 4.74-4.86 (m, 1 H) 6.14 (br d, 1 H) 7.33-7.40 (m,F) 2 H) 7.42-7.51 (m, 4 H) A03 1H NMR (400 MHz, CDCl3) δ ppm 2.48 (s, 3H) 19F NMR (377 MHz, 3.70 (d, 2 H) 4.06-4.19 (m, 3 H) 4.44 (t, 2 H) 4.54(s, 2 H) CDCl3) δ ppm −113.42 (s, 3 4.89-4.99 (m, 1 H) 6.22 (br d, 1 H)7.43-7.48 (m, 1 F) −79.57 (s, 1 F) H) 7.52-7.57 (m, 2 H) 7.60 (d, 2 H)A04 1H NMR (400 MHz, CDCl3) δ ppm 1.36 (d, 6 H) 19F NMR (377 MHz, 2.48(s, 3 H) 3.13 (m, 1 H) 3.70 (d, 1 H) 4.00-4.14 (m, 3 CDCl3) δ ppm−113.46 (s, 1 H) 4.21 (t, 2 H) 4.90-4.99 (m, 1 H) 6.24 (br d, 1 H) F)−79.57 (s, 3 F) 7.41-7.47 (m, 1 H) 7.50-7.56 (m, 2 H) 7.60 (d, 2 H) A051H NMR (400 MHz, CDCl3) δ ppm 1.38 (t, 3 H) 19F NMR (377 MHz, 2.48 (s, 3H) 3.00 (q, 2 H) 3.70 (d, 1 H) 4.01 (dd, 2 H) CDCl3) δ ppm −113.45 (s, 14.06-4.13 (m, 1 H) 4.18-4.26 (m, 2 H) 4.86-4.98 (m, 1 F) −79.57 (s, 3 F)H) 6.27 (br d, 1 H) 7.41-7.47 (m, 1 H) 7.50-7.56 (m, 2 H) 7.60 (d, 2 H)A06 1H NMR (400 MHz, CDCl3) δ ppm 2.45 (s, 3 H) 19F NMR (377 MHz, 3.70(d, 1 H) 3.82 (q, 2 H) 4.04-4.18 (m, 3 H) 4.35 (t, 2 H) CDCl3) δ ppm−113.41 (s, 1 4.80-4.92 (m, 1 H) 6.37 (d, 1 H) 7.38-7.43 (m, 1 H) F)−79.62 (s, 3 F) −61.97 (s, 7.48-7.53 (m, 2 H) 7.59 (d, 2 H) 3 F) A07 1HNMR (400 MHz, CDCl3) δ ppm 2.48 (s, 3 H) 19F NMR (377 MHz, 2.93 (s, 3 H)3.70 (br d, 1 H) 3.97-4.15 (m, 3 H) 4.24 (t, 2 CDCl3) δ ppm −79.42 (s, 3H) 4.81-4.94 (m, 1 H) 6.25 (br d, 1 H) 7.41-7.48 (m, F) 1 H) 7.51-7.58(m, 2 H) 7.65 (s, 2 H) A08 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.45 (s, 319F NMR (376 MHz, H) 4.17-4.28 (m, 3 H) 4.33-4.44 (m, 3 H) Solvent) δppm −80.6 (s, 3 4.83-4.95 (m, 1 H) 5.48 (d, 2 H) 7.53-7.58 (m, 1 H) F)−214.0 (s, 1 F) 7.63-7.69 (m, 5 H) 8.24 (br d, 1 H) A09 1H NMR (400 MHz,CDCl3) δ ppm 2.45 (s, 3 H) 19F NMR (377 MHz, 3.71 (d, 1 H) 4.08 (d, 1 H)4.24 (m, 2 H) 4.56 (t, 2 H) CDCl3) δ ppm −79.54 (s, 3 4.90-5.02 (m, 1 H)6.41 (br d, 1 H) 7.39-7.47 (m, 2 H) F) −75.41 (s, 3 F) 7.48-7.58 (m, 4H) A10 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.45 (s, 3 19F NMR (376 MHz,H) 4.21-4.31 (m, 1 H) 4.36-4.46 (m, 3 H) 4.60 (t, 2 ACETONE-d6) δ ppm H)4.98-5.10 (m, 1 H) 7.54-7.60 (m, 1 H) −76.9 (s, 3 F) −80.3 (s, 3 F)7.61-7.69 (m, 2 H) 7.84 (s, 2 H) 8.34 (br d, 1 H) A11 1H NMR (400 MHz,CDCl3) δ ppm 1.33 (t, 3 H) 19F NMR (377 MHz, 2.44 (s, 3 H) 2.96 (q, 2 H)3.71 (d, 1 H) 3.98-4.22 (m, 5 H) CDCl3) δ ppm −79.54 (s, 3 4.85-4.98 (m,1 H) 6.55 (d, 1 H) 7.39-7.46 (m, 2 H) F) 7.48-7.54 (m, 4 H) A12 1H NMR(400 MHz, CDCl3) δ ppm 2.45 (s, 3 H) 19F NMR (377 MHz, 3.70 (d, 1 H)4.05-4.12 (m, 1 H) 4.17-4.26 (m, 2 H) CDCl3) δ ppm −121.02 (s, 2 4.51(t, 2 H) 4.89-5.02 (m, 1 H) 6.20 (t, 1 H) 6.43 (d, 1 H) F) −113.39 (s, 1F) −79.62 (s, 7.38-7.45 (m, 1 H) 7.48-7.54 (m, 2 H) 7.59 (d, 2 H) 3 F)A13 1H NMR (400 MHz, CDCl3) δ ppm 1.23-1.36 (m, 3 19F NMR (377 MHz, H)2.41 (s, 3 H) 2.93 (q, 2 H) 3.72 (d, 1 H) CDCl3) δ ppm −79.52 (s, 33.99-4.21 (m, 5 H) 4.91 (m, 1 H) 6.84 (d, 1 H) 7.34-7.41 (m, 1 F) H)7.46 (m, 2 H) 7.65 (s, 2 H) A14 1H NMR (400 MHz, CDCl3) δ ppm 2.44 (s, 3H) 19F NMR (377 MHz, 3.70 (d, 1 H) 4.05-4.15 (m, 1 H) 4.21 (dd, 2 H)4.51 (t, 2 CDCl3) δ ppm −121.05 (s, 2 H) 4.90-5.01 (m, 1 H) 6.20 (t, 1H) 6.54 (br d, 1 H) F) −79.47 (s, 3 F) 7.39-7.44 (m, 1 H) 7.48-7.54 (m,2 H) 7.63-7.67 (m, 2 H) A15 1H NMR (400 MHz, CDCl3) δ ppm 2.44 (s, 3 H)19F NMR (377 MHz, 3.70 (d, 1 H) 4.04-4.16 (m, 1 H) 4.20-4.28 (m, 2 H)CDCl3) δ ppm −113.37 (s, 1 4.55 (t, 2 H) 4.90-5.01 (m, 1 H) 6.47 (br d,2 H) F) −79.62 (s, 3 F) −75.45 (s, 7.37-7.45 (m, 1 H) 7.48-7.54 (m, 2 H)7.59 (d, 2 H) 3 F) A16 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.44 (s, 3 19FNMR (376 MHz, H) 4.16-4.29 (m, 3 H) 4.29-4.45 (m, 3 H) ACETONE-d6) δ ppm4.82-4.97 (m, 1 H) 5.47 (d, 2 H) 7.53-7.58 (m, 1 H) −80.3 (s, 3 F)−214.0 (s, 1 F) 7.62-7.68 (m, 2 H) 7.84 (s, 2 H) 8.24 (br d, 1 H) A17 1HNMR (400 MHz, ACETONE-d6) δ ppm 2.48 (s, 3 19F NMR (376 MHz, H) 4.24(dd, 2 H) 4.30-4.43 (m, 3 H) 4.46-4.53 (m, ACETONE-d6) δ ppm 1 H)4.86-4.97 (m, 1 H) 5.51 (d, 2 H) 7.56-7.61 (m, −63.3 (s, 3 F) −80.4 (s,3 F) 1 H) 7.65-7.71 (m, 2 H) 7.94-8.00 (m, 2 H) 8.03 (s, −214.0 (s, 1 F)1 H) 8.27 (br d, 1 H) A18 1H NMR (400 MHz, CDCl3) δ ppm 1.30 (t, 3 H)19F NMR (377 MHz, 2.43 (s, 3 H) 2.93 (q, 2 H) 3.74 (d, 1 H) 3.99-4.07(m, 2 H) CDCl3) δ ppm −79.68 (s, 3 4.10-4.21 (m, 3 H) 4.85-4.98 (m, 1 H)6.72 (d, 1 H) F) −62.81 (s, 3 F) 7.37-7.43 (m, 1 H) 7.47-7.53 (m, 2 H)7.70 (s, 1 H) 7.76 (s, 1 H) 7.82 (s, 1 H) A19 1H NMR (400 MHz,ACETONE-d6) δ ppm 2.45 (s, 3 19F NMR (376 MHz, H) 2.96 (s, 3 H)3.96-4.07 (m, 2 H) 4.15-4.24 (m, 2 ACETONE-d6) δ ppm H) 4.26-4.37 (m, 1H) 4.37-4.53 (m, 1 H) 4.82 (q, 1 −63.3 (s, 3 F) −80.4 (s, 3 F) H) 7.55(d, 1 H) 7.63-7.68 (m, 2 H) 7.92-7.97 (m, 2 H) 8.00 (s, 1 H) 8.17 (br d,1 H) A20 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.45 (s, 3 19F NMR (376 MHz,H) 4.17-4.30 (m, 3 H) 4.32-4.44 (m, 3 H) ACETONE-d6) δ ppm 4.83-4.97 (m,1 H) 5.48 (d, 2 H) 7.53-7.59 (m, 1 H) −80.5 (s, 3 F) −116.3 (s, 1 F)7.59-7.70 (m, 2 H) 7.80 (d, 2 H) 8.24 (br d, 1 H) −214.1 (s, 1 F) A21 1HNMR (400 MHz, CDCl3) δ ppm 2.43 (s, 3 H) 19F NMR (377 MHz, 3.71 (d, 1 H)4.04-4.15 (m, 1 H) 4.17-4.26 (m, 2 H) CDCl3) δ ppm −121.04 (s, 2 4.50(t, 2 H) 4.90-5.01 (m, 1 H) 6.06 (t, 1 H) 6.54 (d, 1 H) F) −79.53 (s, 3F) 7.37-7.46 (m, 2 H) 7.47-7.54 (m, 4 H) A22 1H NMR (400 MHz, CDCl3) δppm 2.46 (s, 3 H) 19F NMR (377 MHz, 3.74 (d, 1 H) 4.12-4.25 (m, 3 H)4.52 (t, 2 H) CDCl3) δ ppm −121.04 (s, 2 4.91-5.00 (m, 1 H) 6.20 (t, 1H) 6.49 (br d, 1 H) 7.43 (d, 1 H) F) −79.64 (s, 3 F) −62.83 (s,7.48-7.58 (m, 2 H) 7.70 (s, 1 H) 7.77 (s, 1 H) 7.83 (s, 3 F) 1 H) A23 1HNMR (400 MHz, CDCl3) δ ppm 2.47 (s, 3 H) 19F NMR (377 MHz, 2.56-2.68 (m,2 H) 3.15-3.22 (m, 2 H) 3.70 (d, 1 H) CDCl3) δ ppm −79.43 (s, 34.01-4.16 (m, 3 H) 4.26 (t, 2 H) 4.86-4.97 (m, 1 H) F) −66.06 (s, 3 F)6.30 (d, 1 H) 7.41-7.46 (m, 1 H) 7.50-7.56 (m, 2 H) 7.65 (s, 2 H) A24 1HNMR (400 MHz, DMSO-d6) δ ppm 2.38 (s, 3 H) 19F NMR (377 MHz, 2.66-2.80(m, 2 H) 3.43-3.50 (m, 2 H) DMSO-d6) δ ppm 3.94-4.03 (m, 2 H) 4.19 (t, 2H) 4.28-4.43 (m, 2 H) −115.23 (s, 1 F) −78.98 (s, 3 F) 4.62-4.76 (m, 1H) 7.49-7.54 (m, 1 H) 7.58-7.67 (m, 2 H) −64.27 (s, 3 F) 7.81 (d, 2 H)9.05 (d, 1 H) A25 1H NMR (400 MHz, CDCl3) δ ppm 2.46 (s, 3 H) 19F NMR(377 MHz, 3.70 (d, 1 H) 3.83 (q, 2 H) 4.05-4.18 (m, 3 H) 4.36 (t, 2 H)CDCl3) δ ppm −79.46 (s, 3 4.81-4.93 (m, 1 H) 6.30 (br d, 1 H) 7.40-7.45(m, 1 F) −61.97 (s, 3 F) H) 7.50-7.56 (m, 2 H) 7.64-7.67 (m, 2 H) A26 1HNMR (400 MHz, DMSO-d6) δ ppm 2.38 (s, 3 H) 19F NMR (377 MHz, 4.09 (br t,2 H) 4.24-4.44 (m, 4 H) 4.64-4.76 (m, 1 DMSO-d₆) δ ppm −78.85 (s, H)5.20 (s, 2 H) 7.51 (br d, 1 H) 7.58-7.66 (m, 2 H) 3 F) 7.84 (s, 2 H)9.08 (br d, 1 H) A27 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 19F NMR (377MHz, 2.45 (s, 3 H) 3.71 (d, 1 H) 4.10 (d, 1 H) 4.13-4.21 (m, 2 H)CHLOROFORM-d) δ ppm 4.36-4.45 (m, 4 H) 4.88-4.99 (m, 1 H) −79.46 (s, 3F) 7.40-7.46 (m, 1 H) 7.46-7.55 (m, 2 H) 7.65 (s, 3 H) A28 1H NMR (400MHz, CHLOROFORM-d) δ ppm 19F NMR (377 MHz, 2.47 (s, 3 H) 3.71 (d, 1 H)4.10 (d, 1 H) 4.17 (dd, 2 H) CHLOROFORM-d) δ ppm 4.36-4.48 (m, 4 H)4.89-4.98 (m, 1 H) 6.34 (br d, 1 H) −79.59 (s, 3 F), −113.42 (s,7.41-7.46 (m, 1 H) 7.50-7.57 (m, 2 H) 7.60 (d, 2 H) 1F)

BIOLOGICAL EXAMPLES

These Examples illustrate the pesticidal/insecticidal properties ofcompounds of formula (Ia).Tests were performed as follows:

Example B1: Diabrotica balteata (Corn Root Worm)

Maize sprouts placed onto an agar layer in 24-well microtiter plateswere treated with aqueous test solutions prepared from 10′000 ppm DMSOstock solutions by spraying. After drying, the plates were infested withL2 larvae (6 to 10 per well). The samples were assessed for mortalityand growth inhibition in comparison to untreated samples 4 days afterinfestation.The following compounds gave an effect of at least 80% in at least oneof the two categories (mortality or growth inhibition) at an applicationrate of 200 ppm:

A01, A02, A03, A04, A05, A06, A07, A08, A09, A10, A11, A12, A13, A14,A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28,B01 Example B2: Euschistus heros(Neotropical Brown Stink Bug)

Soybean leaves on agar in 24-well microtiter plates were sprayed withaqueous test solutions prepared from 10′000 ppm DMSO stock solutions.After drying the leaves were infested with N2 nymphs. The samples wereassessed for mortality and growth inhibition in comparison to untreatedsamples 5 days after infestation.The following compounds gave an effect of at least 80% in at least oneof the two categories (mortality or growth inhibition) at an applicationrate of 200 ppm:

A01, A02, A03, A04, A05, A06, A07, A08, A09, A10, A11, A12, A13, A14,A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28,B01 Example B3: Myzus persicae (Green Peach Aphid). Intrinsic Activity

Test compounds prepared from 10′000 ppm DMSO stock solutions wereapplied by pipette into 24-well microtiter plates and mixed with sucrosesolution. The plates were closed with a stretched Parafilm. A plasticstencil with 24 holes was placed onto the plate and infested peaseedlings were placed directly on the Parafilm. The infested plate wasclosed with a gel blotting paper and another plastic stencil and thenturned upside down. The samples were assessed for mortality 5 days afterinfestation.The following compounds resulted in at least 80% mortality at a testrate of 12 ppm:

A01, A02, A03, A04, A05, A06, A07, A08, A09, A10, A11, A12, A13, A14,A15, A16, A17, A18, A19, A20, A21, A22 Example B4: Plutella xylostella(Diamond Back Moth)

24-well microtiter plates with artificial diet were treated with aqueoustest solutions prepared from 10′000 ppm DMSO stock solutions bypipetting. After drying, the plates were infested with L2 larvae (10 to15 per well). The samples were assessed for mortality and growthinhibition in comparison to untreated samples 5 days after infestation.The following compounds gave an effect of at least 80% in at least oneof the two categories (mortality or growth inhibition) at an applicationrate of 200 ppm:

A01, A02, A03, A04, A05, A06, A07, A08, A09, A10, A11, A12, A13, A14,A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28,B01 Example B5: Spodoptera littoralis (Egyptian Cotton Leaf Worm):Feeding/Contact Activity

Cotton leaf discs were placed onto agar in 24-well microtiter plates andsprayed with aqueous test solutions prepared from 10′000 ppm DMSO stocksolutions. After drying the leaf discs were infested with five L1larvae. The samples were assessed for mortality 3 days afterinfestation.The following compounds resulted in at least 80% mortality at anapplication rate of 200 ppm:

A01, A02, A03, A04, A05, A06, A07, A08, A09, A10, A11, A12, A13, A14,A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28,B01 Example B6: Tetranychus urticae (Two-Spotted Spider Mite):Feeding/Contact Activity

Bean leaf discs on agar in 24-well microtiter plates were sprayed withaqueous test solutions prepared from 10′000 ppm DMSO stock solutions.After drying the leaf discs were infested with a mite population ofmixed ages. The samples were assessed for mortality on mixed population(mobile stages) 8 days after infestation.The following compounds resulted in at least 80% mortality at anapplication rate of 200 ppm:

A01, A02, A03, A04, A05, A06, A07, A08, A09, A10, A11, A12, A13, A14,A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28,B01 Example B7: Thrips tabaci (Onion Thrips) Feeding/Contact Activity

Sunflower leaf discs were placed on agar in 24-well microtiter platesand sprayed with aqueous test solutions prepared from 10′000 ppm DMSOstock solutions. After drying the leaf discs were infested with a thripspopulation of mixed ages. The samples were assessed for mortality 6 daysafter infestation.The following compounds resulted in at least 80% mortality at anapplication rate of 200 ppm:

A01, A02, A03, A04, A05, A06, A07, A08, A09, A10, A11, A12, A13, A14,A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28,B01 Example B8: Myzus persicae (Green Peach Aphid). Feeding/ContactActivity

Sunflower leaf discs were placed onto agar in a 24-well microtiter plateand sprayed with aqueous test solutions prepared from 10′000 ppm DMSOstock solutions. After drying, the leaf discs were infested with anaphid population of mixed ages. The samples were assessed for mortality6 days after infestation.The following compounds resulted in at least 80% mortality at anapplication rate of 200 ppm:

A01, A03, A04, A05, A06, A07, A08, A09, A12, A13, A14, A15, A16, A17,A18, A21, A22, A26, A27, A28, B01. COMPARATIVE EXAMPLES

Compounds of the invention were tested alongside a number of compoundsfrom WO 2013/026931.

Example C1: Plutella xylostella (Diamond Back Moth): Feeding/ContactActivity

24-well microtiter plates with artificial diet were treated with aqueoustest solutions prepared from 10′000 ppm DMSO stock solutions bypipetting. After drying, the plates were infested with L2 larvae (10 to15 per well). The samples were assessed for mortality (%) 5 days afterinfestation at the various application rates.

Example C2: Spodoptera littoralis (Egyptian Cotton Leaf Worm):Feeding/Contact Activity

Cotton leaf discs were placed onto agar in 24-well microtiter plates andsprayed with aqueous test solutions prepared from 10′000 ppm DMSO stocksolutions. After drying the leaf discs were infested with five L1larvae. The samples were assessed for mortality (%) 3 days afterinfestation at the various application rates.Example C3: Tetranychus urticae (Two-Spotted Spider Mite):Feeding/Contact ActivityBean leaf discs on agar in 24-well microtiter plates were sprayed withaqueous test solutions prepared from 10′000 ppm DMSO stock solutions.After drying the leaf discs were infested with a mite population ofmixed ages. The samples were assessed for mortality on mixed population(%) (mobile stages) 8 days after infestation at the various applicationrates.

Example C4: Thrips tabaci (Onion Thrips) Feeding/Contact Activity

Sunflower leaf discs were placed on agar in 24-well microtiter platesand sprayed with aqueous test solutions prepared from 10′000 ppm DMSOstock solutions. After drying the leaf discs were infested with a thripspopulation of mixed ages. The samples were assessed for mortality (%) 6days after infestation at the various application rates.Results of Examples C₁ to C₄ are shown in Table D below:

TABLE D Plutella Tetranychus Spodoptera xylostella Thrips tabaci urticaelittoralis larval mixed mixed larval average population populationapplication average mortality average average Compound/Test sytem rate(ppm) mortality (%) (%) mortality (%) mortality (%) WO 2013/026931 200100 100 100 100 Compound A206 50 100 100 100 100 12.5 100 100 0 100 3.120 100 80 0.781 0 80 0 0.195 0 0 0 WO 2013/026931 200 100 100 0 80Compound A205 50 0 100 0 80 12.5 0 100 0 80 3.12 0 100 50 0.781 0 0 00.195 0 0 0 WO 2013/026931 200 100 100 90 100 Compound A197 50 100 10090 100 12.5 73 80 0 50 3.12 0 0 0.781 0 0 WO 2013/026931 200 100 100 90100 Compound A196 50 100 87 80 100 12.5 100 80 40 73 3.12 0 0 0 0.781 00 0 WO 2013/026931 200 100 100 100 100 Compound A195 50 50 100 65 10012.5 0 90 0 58 3.12 25 0 0.781 0 0 Compound A02 200 100 100 100 100 50100 100 100 100 12.5 100 100 100 100 3.12 100 100 100 100 0.781 100 100100 50 0.195 50 80 0 0It can clearly be seen from Table D that the compound of the inventionshows improved activity over the compounds from WO 2013/026931 in all ofthe tests.

What is claimed is:
 1. A compound of formula (I),

wherein A¹, A², A³ and A⁴, independently of one another, are C—H, C—R⁵or nitrogen; R¹ is hydrogen, C₁-C₈alkyl, C₁-C₈alkylcarbonyl-,C₁-C₈alkoxy, C₁-C₈alkoxy-C₁-C₈alkyl or C₁-C₈alkoxycarbonyl; R² isC₁-C₈alkyl or C₁-C₈haloakyl; R³ is C₁-C₈haloalkyl; R⁴ is aryl, arylsubstituted by one to three R⁷, heteroaryl or heteroaryl substituted byone to three R⁷; each R⁵ is independently halogen, cyano, nitro,C₁-C₈alkyl, C₃-C₈cycloalkyl, C₁-C₈haloalkyl, C₂-C₈alkenyl,C₂-C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, C₁-C₈alkoxy,C₁-C₈haloalkoxy, or C₁-C₈alkoxycarbonyl-, or two R⁵ on adjacent carbonatoms together form a —CH₂—CH₂—CH₂— bridge, a —CH═CH—CH═CH— bridge or a—N═CH—CH═CH— bridge; and each R⁷ is independently halogen, cyano, nitro,C₁-C₈alkyl, C₁-C₈haloalkyl, C₁-C₈alkoxy or C₁-C₈haloalkoxy; andagrochemically acceptable salts, stereoisomers, enantiomers, tautomersand N-oxides of those compounds.
 2. A compound of formula (I) accordingto claim 1, wherein R¹ is hydrogen, C₁-C₈alkyl, C₁-C₈alkylcarbonyl- orC₁-C₈alkoxycarbonyl.
 3. A compound of formula (I) according to claim 1,wherein R² is C₁-C₄alkyl or C₁-C₄haloalkyl.
 4. A compound of formula (I)according to claim 1, wherein R³ is is C₁-C₄haloalkyl.
 5. A compound offormula (I) according to claim 1, wherein R⁴ is phenyl, phenylsubstituted by one to three R⁷.
 6. A compound of formula (I) accordingto claim 1, wherein each R⁵ is independently halogen, cyano, nitro,C₁-C₈alkyl, C₂-C₈ alkenyl, C₃-C₈cycloalkyl, or C₁-C₈haloalkyl.
 7. Acompound of formula (I) according to claim 1, wherein each R⁷ isindependently Cl, Br, F or CF₃.
 8. A compound of formula (I) accordingto claim 1, wherein A¹ is C—R⁵, A², A³ and A⁴ are C—H.
 9. A compound offormula (Int-I)

wherein A¹, A², A³, A⁴, R² and R¹ are as defined for a compound offormula (I) and R⁶ is hydrogen or S(O)₂R² and X^(B) is a halogen, orX^(B) is cyano, formyl, CH═N—OH or acetyl; and a salt or N-oxidethereof.
 10. A compound of formula (Int-II)

wherein A¹, A², A³, A⁴, R² and R¹ are as defined for a compound offormula (I); R⁶ is hydrogen or S(O)₂R² and X^(C) is CH₂-halogen, whereinhalogen is bromo or chloro, CH═C(R³)R⁴ or CH₂C(OH)(R³)R⁴ wherein R³ andR⁴ are as defined for a compound of formula (I); and a salt or N-oxidethereof.
 11. A compound of formula (Int-III)

wherein A¹, A², A³, A⁴, R¹, R³ and R⁴ are as defined for a compound offormula (I) and R⁶ is hydrogen; and a salt or N-oxide thereof.
 12. Apesticidal composition, which comprises at least one compound of formula(I) according to claim 1 or, where appropriate, a tautomer thereof, ineach case in free form or in agrochemically utilizable salt form, asactive ingredient and at least one auxiliary.
 13. A method forcontrolling pests, which comprises applying a composition according toclaim 12 to the pests or their environment with the exception of amethod for treatment of the human or animal body by surgery or therapyand diagnostic methods practised on the human or animal body.
 14. Amethod for the protection of seeds from the attack by pests, whichcomprises treating the seeds or the site, where the seeds are planted,with a composition according to claim 12.